[ CAS No. 930782-89-1 ] {[proInfo.proName]}

Name: 930782-89-1|(R)-4-Benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate|97%
Brand: Ambeed
SKU: A824265
Rating: 99 (40 reviews)

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2D 3D

Structure of 930782-89-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 930782-89-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 930782-89-1 ]

SDS Specification

Alternatived Products of [ 930782-89-1 ]

Product Details of [ 930782-89-1 ]

CAS No. :	930782-89-1	MDL No. :	MFCD17676317
Formula :	C₁₈H₂₆N₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OKWDDQLIGHSFEA-OAHLLOKOSA-N
M.W :	350.41	Pubchem ID :	16124590
Synonyms :

Calculated chemistry of [ 930782-89-1 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	8
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	100.34
TPSA :	79.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.49
Log Po/w (XLOGP3) :	1.66
Log Po/w (WLOGP) :	1.32
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	1.04
Consensus Log Po/w :	1.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.71
Solubility :	0.686 mg/ml ; 0.00196 mol/l
Class :	Soluble
Log S (Ali) :	-2.94
Solubility :	0.403 mg/ml ; 0.00115 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.73
Solubility :	0.649 mg/ml ; 0.00185 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.49

Safety of [ 930782-89-1 ]

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

Application In Synthesis of [ 930782-89-1 ]

* 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 [ 930782-89-1 ]
Downstream synthetic route of [ 930782-89-1 ]

[ 930782-89-1 ] Synthesis Path-Upstream 1~2

1
[ 930782-89-1 ]
[ 169448-87-7 ]

Reference： [1] Patent: US2018/127370, 2018, A1, . Location in patent: Paragraph 0681; 0679

2
[ 138775-02-7 ]
[ 930782-89-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In 1,2-dimethoxyethane at 0℃; for 0.333333 h; Stage #2: With sodium tetrahydroborate In 1,2-dimethoxyethane; water at 20℃;	(2i?)-4-[(Benzyloxy)carbonyl]-l-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.4 g, 3.9 mmol) was dissolved in dimethoxyethane (10 mL) and to the cooled resultant solution was added N-methylmorpholine (0.4 g, 3.9 mmol) followed by isobutyl chloroformate (0.54 g, 3.9 mmol) by means of drops. The mixture was stirred at 0°C for 20 min and then the mixture was filtered. The filtrate was transferred to a 500 mL flask and then cooled again. Sodium borohydride (0.22 g, 5.9 mmol) dissolved in water (5 mL) was added and the external cooling bath was removed. The reaction mixture was stirred until the temperature of it had reached RT whereupon water (120 mL) was added. The mixture was extracted trice with ethyl acetate and the combined organic solutions were dried and then evaporated. The product was purified by column chromatography on silica gel (ethyl acetate - heptane 10percent to 70percent). There was obtained 1.2 g (84percent) of 4-benzyl 1-tert-butyl (2i?)-2-(hydroxymethyl)piperazine-l,4-dicarboxylate as a colorless oil. ¹HNMR (500 MHz, CDCl₃): 1.4 (s, 9H), 2.7-3.2 (b, 4H), 3.5 (b, 2H), 3.8-4.2 (m, 4H), 5.1 (m, 2H)₅ 7.2- 7.4 (m, 5H); LCMS: m/z 349 (M-I)

Reference： [1] Patent: WO2007/37743, 2007, A1, . Location in patent: Page/Page column 47

[ 930782-89-1 ] Synthesis Path-Downstream 1~51

1
[ 138775-02-7 ]
[ 930782-89-1 ]

Yield	Reaction Conditions	Operation in experiment
84%		(2i?)-4-[(Benzyloxy)carbonyl]-l-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.4 g, 3.9 mmol) was dissolved in dimethoxyethane (10 mL) and to the cooled resultant solution was added N-methylmorpholine (0.4 g, 3.9 mmol) followed by isobutyl chloroformate (0.54 g, 3.9 mmol) by means of drops. The mixture was stirred at 0C for 20 min and then the mixture was filtered. The filtrate was transferred to a 500 mL flask and then cooled again. Sodium borohydride (0.22 g, 5.9 mmol) dissolved in water (5 mL) was added and the external cooling bath was removed. The reaction mixture was stirred until the temperature of it had reached RT whereupon water (120 mL) was added. The mixture was extracted trice with ethyl acetate and the combined organic solutions were dried and then evaporated. The product was purified by column chromatography on silica gel (ethyl acetate - heptane 10% to 70%). There was obtained 1.2 g (84%) of 4-benzyl 1-tert-butyl (2i?)-2-(hydroxymethyl)piperazine-l,4-dicarboxylate as a colorless oil. 1HNMR (500 MHz, CDCl3): 1.4 (s, 9H), 2.7-3.2 (b, 4H), 3.5 (b, 2H), 3.8-4.2 (m, 4H), 5.1 (m, 2H)5 7.2- 7.4 (m, 5H); LCMS: m/z 349 (M-I)
	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃;	(2,S)-4-Benzyloxycarbonyl-l-/er/-butoxycarbonyl-piperazine-2-carboxylic acid (5.0 g, 13.72 mmol) was dissolved in anhydrous THF (70 mL) and cooled to 0 C with an ice bath. Borane dimethyl sulfide complex (2.6 mL, 27.44 mmol) was added dropwise at 0 C, slowly. Then the reaction solution was left to warm up to room temperature and stirred overnight. The reaction mixture was then cooled to 0 C with an ice bath and quenched with water, dropwise, and extracted with EtOAc. The aqueous phase was extracted with DCM (2x). Combined organic layers were dried over anhydrous MgS04, filtered and evaporated under reduced pressure. It was used without further purification.

Reference： [1]Patent: WO2007/37743,2007,A1 .Location in patent: Page/Page column 47
[2]Patent: WO2019/183133,2019,A1 .Location in patent: Page/Page column 38; 39

2
[ 930782-89-1 ]
(R)-tert-butyl 4-(5-(1-(2-cyanophenyl)piperidin-4-ylamino)-2,4-dimethylbenzoyl)-2-(hydroxymethyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/127370,2018,A1

3
[ 930782-89-1 ]
[ 169448-87-7 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 4.0h;	Step 1: (R)-tert-Butyl-2-(hydroxyethyl)piperazine-1-carboxylate (R)-4-Benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate (2.00 g, 4.85 mmol) was dissolved in MeOH (50.00 mL), Pd/C (480.00 mg, 3.95 mmol) was added and stirred at rt for 4 h under H2. The reaction mixture was filtered and the filtrate was concentrated to give crude (R)-tert-butyl-2-(hydroxymethyl)piperazine-1-carboxylate (900.00 mg, 4.16 mmol, 85%) as a colorless oil. ESI-MS (EI+, m/z): 217.3 [M+H]+.

Reference： [1]Patent: US2018/127370,2018,A1 .Location in patent: Paragraph 0681; 0679

4
[ 930782-89-1 ]
(R)-2-(4-(5-(3-(hydroxymethyl)piperazine-1-carbonyl)-2,4-dimethylphenylamino)piperidin-1-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: US2018/127370,2018,A1

5
[ 930782-89-1 ]
N-((1S)-3-(3-(((4-(1,3-dioxoisoindolin-2-yl)butyl)(pyridin-2-ylmethyl)amino)methyl)piperazin-1-yl)-1-phenylpropyl)-4,4-difluorocyclohexane-1-carboxamide [ No CAS ]