[ CAS No. 57850-17-6 ] {[proInfo.proName]}

Name: 57850-17-6|Z-Trp-Trp-OH|97%
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Quality Control of [ 57850-17-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 57850-17-6 ]

CAS No. :	57850-17-6	MDL No. :	MFCD00022760
Formula :	C₃₀H₂₈N₄O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IGVSKBFIFVGVSE-SVBPBHIXSA-N
M.W :	524.57	Pubchem ID :	14160293
Synonyms :

Safety of [ 57850-17-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 57850-17-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 57850-17-6 ]
Downstream synthetic route of [ 57850-17-6 ]

[ 57850-17-6 ] Synthesis Path-Upstream 1~8

1
[ 17689-58-6 ]
[ 57850-17-6 ]

Yield	Reaction Conditions	Operation in experiment
87.3%	Stage #1: for 2 h; Stage #2: With hydrogenchloride In water	The saponification method of McDermott et al., Journal of theAmerican Chemical Society 1982, 104, 3002-3007 was used. The diprotected dipeptide (0.425g, 0.79 mmol) was dissolved in MeOH (2OmL) and 1 N NaOH (5 mL) was added to the solution. On occasion, the reaction was performed on double or triple this scale without difficulty. The reaction was stirred and monitored by TLC. After 2 hrs., water (20 mL) was added and unreacted compound was removed by washing with ether (2x20 mL). The aqueous layer was then acidified to pH 2 with cone. HCl and EtOAc was quickly added (20 mL). The EtOAc layer was separated and the aqueous layer extracted with two more portions of EtOAc (20 mL). The extracts were dried over MgSψ4, concentrated and the resulting oil was recrystallized from EtOAc/hexanes and then from MeOH/HO. The white solid obtained was dried in vacuo. EPO <DP n="130"/>CBZ-Trp-Trp-OH[00436] CBZ-L-Trp-L-Trp-OH[00437] White solid (0.257g, 87.3percent); mp 207-210⁰C (lit.209-210⁰C); [α]_D²⁵+19.2, c 0.8, AcOH (lit. +23.7, c 0.8, AcOH); TLC (R₁) A: 0.74, B: 0.69; IR (v_max): 3412 (NH), 3372 (NH), 3334 (NH), 3054 (CH, aromatic), 2921 (CH), 1729 (COOH), 1695 (C=O), 1659 (C=O), 1515 (C=C, aromatic) cm^"1; ¹HNMR: δ: 2.90 (dd, IH, H_c, J=I 1.7 Hz, J=12.1 Hz), 3.21 (m, 3H, 2H_F and HcO, 4.35 (m, IH, H₈), 4.54 (m, IH, H_E), 4.94 (s, 2H, Z-CH₂), 7.2 (m, 14H, 13Ar-H and H_A), 7.56 (d, IH, Ar-H, J=7.4 Hz), 7.65 (d, IH, Ar-H, J=7.5 Hz), 8.29 (d, IH, H_D, J=7.1 Hz), 10.82 (s, IH, indole N- H), 10.90 (s, IH, indole N-H), 12.64 (bs, IH, CO₂-H); ¹³C NMR: 28.02, 28.69, 53.82, 56.19, 66.09, 110.49, 111.05, 112.16 (2C), 116.70 (2C), 119.04, 119.25, 119.42 (2C), 121.68, 121.78, 124.69 (2C), 128.12, 128.31, 128.51, 129.15, 136.91, 137.81, 153. 21 (2C), 156.64, 172.81, 174.13; FAB (m/z): 525.2 [M+H]⁺.

Reference： [1] Patent: WO2006/125324, 2006, A1, . Location in patent: Page/Page column 128-129
[2] Tetrahedron Letters, 1982, vol. 23, # 19, p. 1985 - 1988

2
[ 850232-59-6 ]
[ 73-22-3 ]
[ 57850-17-6 ]

Reference： [1] Tetrahedron, 2009, vol. 65, # 25, p. 4923 - 4929
[2] Synthesis, 2006, # 3, p. 411 - 424

3
[ 7432-21-5 ]
[ 57850-17-6 ]

Reference： [1] Synthesis, 2006, # 3, p. 411 - 424
[2] Journal of the American Chemical Society, 1980, vol. 102, # 13, p. 4537 - 4538
[3] Tetrahedron Letters, 1982, vol. 23, # 19, p. 1985 - 1988
[4] Journal of Biological Chemistry, 1948, vol. 175, p. 39,46

4
[ 73-22-3 ]
[ 57850-17-6 ]
[ 52023-39-9 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 13, p. 4537 - 4538

5
[ 4299-70-1 ]
[ 57850-17-6 ]

Reference： [1] Tetrahedron Letters, 1982, vol. 23, # 19, p. 1985 - 1988

6
[ 501-53-1 ]
[ 57850-17-6 ]

Reference： [1] Journal of Biological Chemistry, 1948, vol. 175, p. 39,46

7
[ 73-22-3 ]
[ 57850-17-6 ]

Reference： [1] Journal of Biological Chemistry, 1948, vol. 175, p. 39,46

8
[ 73-22-3 ]
[ 64693-64-7 ]
[ 57850-17-6 ]

Reference： [1] Journal of Biological Chemistry, 1948, vol. 175, p. 39,46

[ 57850-17-6 ] Synthesis Path-Downstream 1~19

1
[ 73-22-3 ]
[ 64693-64-7 ]
[ 57850-17-6 ]

Reference： [1]Journal of Biological Chemistry,1948,vol. 175,p. 39,46

2
[ 40216-93-1 ]
[ 57850-17-6 ]
[ 82989-13-7 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 1985 - 1988

3
[ 17689-58-6 ]
[ 57850-17-6 ]

Yield	Reaction Conditions	Operation in experiment
87.3%		The saponification method of McDermott et al., Journal of theAmerican Chemical Society 1982, 104, 3002-3007 was used. The diprotected dipeptide (0.425g, 0.79 mmol) was dissolved in MeOH (2OmL) and 1 N NaOH (5 mL) was added to the solution. On occasion, the reaction was performed on double or triple this scale without difficulty. The reaction was stirred and monitored by TLC. After 2 hrs., water (20 mL) was added and unreacted compound was removed by washing with ether (2x20 mL). The aqueous layer was then acidified to pH 2 with cone. HCl and EtOAc was quickly added (20 mL). The EtOAc layer was separated and the aqueous layer extracted with two more portions of EtOAc (20 mL). The extracts were dried over MgSθ4, concentrated and the resulting oil was recrystallized from EtOAc/hexanes and then from MeOH/HO. The white solid obtained was dried in vacuo. EPO <DP n="130"/>CBZ-Trp-Trp-OH[00436] CBZ-L-Trp-L-Trp-OH[00437] White solid (0.257g, 87.3%); mp 207-2100C (lit.209-2100C); [α]D25+19.2, c 0.8, AcOH (lit. +23.7, c 0.8, AcOH); TLC (R1) A: 0.74, B: 0.69; IR (vmax): 3412 (NH), 3372 (NH), 3334 (NH), 3054 (CH, aromatic), 2921 (CH), 1729 (COOH), 1695 (C=O), 1659 (C=O), 1515 (C=C, aromatic) cm"1; 1HNMR: δ: 2.90 (dd, IH, Hc, J=I 1.7 Hz, J=12.1 Hz), 3.21 (m, 3H, 2HF and HcO, 4.35 (m, IH, H8), 4.54 (m, IH, HE), 4.94 (s, 2H, Z-CH2), 7.2 (m, 14H, 13Ar-H and HA), 7.56 (d, IH, Ar-H, J=7.4 Hz), 7.65 (d, IH, Ar-H, J=7.5 Hz), 8.29 (d, IH, HD, J=7.1 Hz), 10.82 (s, IH, indole N- H), 10.90 (s, IH, indole N-H), 12.64 (bs, IH, CO2-H); 13C NMR: 28.02, 28.69, 53.82, 56.19, 66.09, 110.49, 111.05, 112.16 (2C), 116.70 (2C), 119.04, 119.25, 119.42 (2C), 121.68, 121.78, 124.69 (2C), 128.12, 128.31, 128.51, 129.15, 136.91, 137.81, 153. 21 (2C), 156.64, 172.81, 174.13; FAB (m/z): 525.2 [M+H]+.

Reference： [1]Patent: WO2006/125324,2006,A1 .Location in patent: Page/Page column 128-129
[2]Tetrahedron Letters,1982,vol. 23,p. 1985 - 1988

4
[ 57850-17-6 ]
{(S)-2-(1H-Indol-3-yl)-1-[4-(1H-indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1265 - 1270

5
C₃₃H₃₀N₄O₄ [ No CAS ]
[ 73-22-3 ]
[ 57850-17-6 ]
[ 52023-39-9 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 4537 - 4538

6
[ 95-14-7 ]
[ 57850-17-6 ]
[ 886981-42-6 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 4923 - 4929
[2]Synthesis,2006,p. 411 - 424

7
[ 850232-59-6 ]
[ 73-22-3 ]
[ 57850-17-6 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 4923 - 4929
[2]Synthesis,2006,p. 411 - 424

8
[ 57850-17-6 ]
(S)-2-{(S)-2-[(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-(1H-indol-3-yl)propionylamino}-3-(1H-indol-3-yl)propanoic acid [ No CAS ]

Reference： [1]Synthesis,2006,p. 411 - 424

9
[ 57850-17-6 ]
(R)-2-{(S)-2-[(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-(1H-indol-3-yl)propionylamino}-3-(1H-indol-3-yl)propanoic acid [ No CAS ]

Reference： [1]Synthesis,2006,p. 411 - 424

10
[ 7432-21-5 ]
[ 57850-17-6 ]

Reference： [1]Synthesis,2006,p. 411 - 424
[2]Journal of the American Chemical Society,1980,vol. 102,p. 4537 - 4538
[3]Tetrahedron Letters,1982,vol. 23,p. 1985 - 1988
[4]Journal of Biological Chemistry,1948,vol. 175,p. 39,46

11
[ 57850-17-6 ]
[ 119645-70-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1265 - 1270

12
[ 4299-70-1 ]
[ 57850-17-6 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 1985 - 1988

13
[ 501-53-1 ]
[ 57850-17-6 ]

Reference： [1]Journal of Biological Chemistry,1948,vol. 175,p. 39,46

14
[ 73-22-3 ]
[ 57850-17-6 ]

Reference： [1]Journal of Biological Chemistry,1948,vol. 175,p. 39,46

15
[ 57850-17-6 ]
[ 20696-60-0 ]

Yield	Reaction Conditions	Operation in experiment
81.1%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 1.0h;	The CBZ group was removed using catalytic hydrogenation. The N- protected dipeptide (0.47Og, 0.89 mmol) was dissolved in MeOH (20 mL) and the system flushed with N2. Next, 10% palladium on charcoal (0.47Og) was added and the system was flushed with N2 followed by H2. The mixture was then stirred vigorously under H2 pressure from a balloon until TLC indicated completion (approximately 1 hour). The solution was filtered and concentrated. The resulting clear oil was recrystallized from MeOH /Et2O /hexanes, and dried in vacuo, giving a white or light pink powder. EPO <DP n="133"/>H-Trp-Trp-OH [00442] The four diastereomers of H-Trp-Tφ-OH in accordance with the present invention were as follows:H-L-Trp-L-Trp-OH[00443] White solid (0.285g, 81.1%); mp 174-1760C (lit. 1860C); [α]D25 -9.0, c0.8, EtOH (lit. -1 1.0 , c 0.426, EtOH);TLC (Rf) B: 0.30, C: 0.71 ; IR (vmax): 3405 (NH), 3059 (CH, aromatic), 2927 (CH), 1668 (C=O), 1600 (C=O), 1522 (C=C, aromatic) cm'1: 1H NMR δ: 2.84 (dd, IH, Hc, J=8.5 Hz, J=14.9 Hz), 3.12 (m, 3H, 2HF and Hc), 3.62 (dd, IH, HB, J=4.4 Hz, J=8.2 Hz), 4.51 (m, IH, HE), 5.9 (bs, 2H, HA), 7.2 (m, 1OH, Ar-H), 8.35 (d, IH, HD, J=7.4 Hz), 10.84 (s, IH, indole N-H), 10.97 (s, IH, indole N-H); 13C NMR: 28.25, 30.37, 54.15, 55.12, 110.24, 110.74, 111.98, 1 12.16, 118.92, 119.06, 1 19.27 (2C), 121.49, 121.71, 124.37, 125.01, 128.19, 128.38, 136.77, 137.09, 173.02, 174.16; FAB (m/z): 391.3 [M+H]+.

Reference： [1]Patent: WO2006/125324,2006,A1 .Location in patent: Page/Page column 131-132

16
[ 57850-17-6 ]
2-amino-<i>N</i>-methoxy-<i>N</i>-methyl-3-phenyl-propionamide; hydrochloride [ No CAS ]
[ 925913-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃;	8.85 g (36.16 mmol) b, 18.97 g (36.16 mmol) Z-Trp-Trp-OH, 4.89 g (36.16 mmol) 1-hydroxybenzotriazo und 9.35 g (72.33 mmol) N,N-diisopropylethylamin were dissolved in 200 ml dry N,N-dimethylformamid. The solution is cooled in an ice bath and 15.09 g (39.78 mmol) O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphat is added in portions while stirring. The solution is stirred over night at room temperature. The solvent is removed in the vacuum, dissolved in ethylacetate and washed with saturated sodiumbicarbonate, 5% citric acid, dried with magnesiumsulfate and concentrated in the vacuum, to obtain 34.59 g crude product. The crude product is purified by flash chromatography on silicagel using (Eluent: dichlormethane:methanol:conz. ammonia =90:10:1 as eluent. Yield 20 g

Reference： [1]Patent: US2007/37753,2007,A1 .Location in patent: Page/Page column 13

17
[ 1057092-60-0 ]
[ 57850-17-6 ]
C₄₂H₄₀N₈O₆ [ No CAS ]
[ 1057092-58-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 4579 - 4588

18
[ 133489-47-1 ]
[ 57850-17-6 ]
[ 925913-34-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 4579 - 4588

19
[ 133657-45-1 ]
[ 57850-17-6 ]
C₄₁H₄₂N₆O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 4579 - 4588

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Ghs Precautionary Statements

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Prevention
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P232	Protect from moisture.
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P234	Keep only in original container.
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P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 57850-17-6 ] {[proInfo.proName]}

Quality Control of [ 57850-17-6 ]

Related Doc. of [ 57850-17-6 ]

Product Details of [ 57850-17-6 ]

Safety of [ 57850-17-6 ]

Application In Synthesis of [ 57850-17-6 ]

[ 57850-17-6 ] Synthesis Path-Upstream 1~8

[ 57850-17-6 ] Synthesis Path-Downstream 1~19

Related Functional Groups of [ 57850-17-6 ]

Aryls

Amides

Amines

Carboxylic Acids

Related Parent Nucleus of [ 57850-17-6 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 57850-17-6 ]

Related Parent Nucleus of
[ 57850-17-6 ]