[ CAS No. 21462-39-5 ] {[proInfo.proName]}

Name: 21462-39-5|(2S,4R)-N-((1S,2S)-2-Chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride|98%
Brand: Ambeed
SKU: A203629
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Quality Control of [ 21462-39-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 21462-39-5 ]

SDS Specification

Alternatived Products of [ 21462-39-5 ]

Product Details of [ 21462-39-5 ]

CAS No. :	21462-39-5	MDL No. :	MFCD07793327
Formula :	C₁₈H₃₄Cl₂N₂O₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AUODDLQVRAJAJM-XJQDNNTCSA-N
M.W :	461.44	Pubchem ID :	16051951
Synonyms :	Clindamycin hydrochloride	Chemical Name :	(2S,4R)-N-((1S,2S)-2-Chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

Calculated chemistry of [ 21462-39-5 ]

Physicochemical Properties

Num. heavy atoms :	28
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.94
Num. rotatable bonds :	8
Num. H-bond acceptors :	6.0
Num. H-bond donors :	4.0
Molar Refractivity :	118.15
TPSA :	127.56 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) :	-7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.96
Log Po/w (WLOGP) :	0.81
Log Po/w (MLOGP) :	0.16
Log Po/w (SILICOS-IT) :	0.65
Consensus Log Po/w :	0.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.04
Solubility :	0.0423 mg/ml ; 0.0000917 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.3
Solubility :	0.0023 mg/ml ; 0.00000499 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-1.2
Solubility :	29.2 mg/ml ; 0.0634 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	5.66

Safety of [ 21462-39-5 ]

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 [ 21462-39-5 ]

* 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 [ 21462-39-5 ]
Downstream synthetic route of [ 21462-39-5 ]

[ 21462-39-5 ] Synthesis Path-Upstream 1~2

1
[ 16684-06-3 ]
[ 21462-39-5 ]

Yield	Reaction Conditions	Operation in experiment
89.5%	With hydrogenchloride In ethanol at 60℃; for 1 h; Large scale	(3) the clindamycin free base down to 60 , slowly dropping hydrogen chloride saturated ethanol solution, adjust the pH to 1, dropAfter the end of crystallization for 1h, stirring down to 6 , stop stirring, standing for 4h, centrifuged by washing the clindamycin hydrochloride alcohol;(4) The clindamycin hydrochloride was dissolved in 16 L of water, concentrated in vacuo, the ethanol was removed, and the solvent was distilled off14.5 L, the residue was dissolved in 16 L of acetone, and then the acetone aqueous solution was added to 55 L of acetone, crystallized, filtered and dried in vacuo to give 6.7 kg of clindamycin hydrochloride in a molar yield of 89.5percent The HPLC purity of clindamycin was 99.7percent.

Reference： [1] Patent: CN106397505, 2017, A, . Location in patent: Paragraph 0018; 0019; 0020; 0021; 0022; 0023-0041

2
[ 21462-39-5 ]
[ 24729-96-2 ]

Reference： [1] Patent: US4849515, 1989, A,

[ 21462-39-5 ] Synthesis Path-Downstream 1~27

1
[ 21462-39-5 ]
(2S,4R)-1-Methyl-4-propyl-pyrrolidine-2-carboxylic acid [(Z)-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propenyl]-amide [ No CAS ]

Reference： [1]Journal of Antibiotics,1997,vol. 50,p. 866 - 873

2
[ 21462-39-5 ]
clindamycin sulfoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium perborate;pH ~ 8 - 9;	A stereospecific method of synthesizing CSO B is set forth in Scheme 2 below. The oxidation of <strong>[21462-39-5]clindamycin hydrochloride</strong> with sodium perborate (NaBO3) at a pH between about 8 and 9 was found to preferentially yield CSO B (MW=440.98). One test of this synthesis method yielded CSO B with about 93% purity by HPLC. A scaled chromatogram of CSO B produced by this process is presented in FIG. 10.
	With (Dichloroiodo)benzene;	A stereospecific method of synthesizing CSO A is set forth in Scheme 1 below. The oxidation of <strong>[21462-39-5]clindamycin hydrochloride</strong> with iodobenzene dichloride was found to preferentially yield CSO A (MW=440.98). One test of this synthesis method yielded CSO A with greater than about 94% purity, as measured by HPLC. A scaled chromatogram of CSO A produced by this process is presented in FIG. 9.

Reference： [1]Patent: US2008/33031,2008,A1 .Location in patent: Page/Page column 8
[2]Patent: US2008/33031,2008,A1 .Location in patent: Page/Page column 8

3
[ 21462-39-5 ]
clindamycin sulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide;sodium tungstate;pH < 1;	Clindamycin sulfone (CSO2) can be prepared directly by the oxidation of <strong>[21462-39-5]clindamycin HCl</strong> with hydrogen peroxide (H2O2), catalyzed by sodium tungstate (NaWO4) at a pH of less than about 1, as shown in Scheme 3 below. In one test, this oxidation method yielded clindamycin sulfone (MW=456.98) with about 95% purity by HPLC. A scaled chromatogram of CSO2 produced by this process is presented in FIG. 11.

Reference： [1]Patent: US2008/33031,2008,A1 .Location in patent: Page/Page column 8

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 17 This example illustrates the use NaOAc.3H2O instead of an alcohol co-solvent in the crystallization of clindamycin free base. A solution was prepared by combining 34.8 ml of 10% aqueous NaOH, 7.07 g NaOAc.3H2O and 144 ml water. The solution was stirred at 400 rpm and maintained at 22+-2 C. A solution of clindamycin hydrochloride was prepared by dissolving 40 g in 120 ml water.
		Amoxicillin trihydrate and clavulanate potassium combination Cephalexin Clindamycin hydrochloride Doxycycline monohydrate Enrofloxacin Methimazole and

5
[ 21462-39-5 ]
[ 24729-96-2 ]

Yield	Reaction Conditions	Operation in experiment
		STEP I Preparation of protected <strong>[21462-39-5]clindamycin hydrochloride</strong>. STR2 Clindamycin hydrochloride is heated with 2,2-dimethoxypropane in a suitable solvent. Upon cooling, the protected <strong>[21462-39-5]clindamycin hydrochloride</strong>, I, is isolated by filtration. Melting point: 16220 to 163 C.

Reference： [1]Patent: US4849515,1989,A

6
[ 7442-07-1 ]
[ 21462-39-5 ]
7(R)-7-(6-aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 16.0h;	To a solution of <strong>[21462-39-5]clindamycin hydrochloride</strong> (460 mg, 1.0mmol) in DMF (5 ml) were added K2CO3 (152 mg, 1.1 mmol) and 6-aminobenzo[d]thiazole-2-thiol (200 mg, 1.1mmol) and stirred at 100 C for 16 h. Then it was concentrated under reduced pressure. The residue was diluted with water and then extracted with ethyl acetate, washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by preparative TLC(CHCl3/CH3OH/28% aq NH4OH=20/1/0.1) to obtain the title compound as a colorless solid (233.3 mg, 41%). [alpha]D27 +129.5 (c 0.45, MeOH); ESI-MS (m/z)571 (M+H)+ as C25H38N4O5S3; TOF-ESI-HRMS (M+H)+ calcd for C25H38N4O5S3: 571.2083, found: 571.2079; 1H NMR (400 MHz, methanold4)delta 0.87-0.96 (m, 3 H), 1.27-1.39 (m, 4 H), 1.50 (d, J=7.1Hz, 3 H),1.75-1.87 (m, 1 H), 1.95-2.01 (m, 1 H), 2.05 (dd, J=10.2, 8.9 Hz, 1 H), 2.17(s, 3 H), 2.13-2.26 (m, 1 H), 2.39 (s, 3 H), 2.98 (dd, J=10.4, 5.0 Hz, 1 H), 3.21(dd, J=8.5, 6.2Hz, 1 H), 3.54 (dd, J=10.2, 3.3 Hz, 1 H), 3.80-3.84 (m, 1 H),4.11 (dd, J=10.2, 5.6 Hz, 1 H), 4.28 (br dd, J=9.2, 0.6Hz, 1 H), 4.30(dq, J=7.1, 3.9Hz, 1 H), 4.65 (dd, J=9.2, 3.9Hz, 1 H), 5.29 (d, J=5.6Hz,1 H), 6.84 (dd, J=8.7, 2.3Hz, 1 H), 7.08 (dd, J=2.3, 0.4Hz, 1 H), 7.57(dd, J=8.7, 0.4Hz, 1 H). For the qualified analytical purpose, the abovecolorless solid was further purified by reverse-phase column chromatography(YMC triart C18, 20× 250mm, RT, 18.9 ml min- 1, 50mM AcONH4/CH3CN=35/65) to obtain the highly purified title compound as acolorless solid.
40%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 16.0h;	Example 45 7-(6-Aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin (compound 409) Potassium carbonate (138 mg, 1 mmol) and 137 mg (0.75 mmol) of 6-aminobenzo[d]thiazole-2-thiol were successively added to a solution of 231 mg (0.5 mmol) of <strong>[21462-39-5]clindamycin hydrochloride</strong> in N,N-dimethylformamide (1 ml), and the mixture was stirred at 90C for 16 hr. The reaction solution was diluted with ethyl acetate and was washed twice with water. The solvent was removed by distillation, and the residue was purified by preparative thin layer chromatography (chloroform: methanol: 28% aqueous ammonia = 20: 1: 0.1) to give 113 mg (yield 40%) of the title compound. Compound (409) produced in Example 45 and 1H-NMR data and MS data on these compounds are shown in Table 21a.

Reference： [1]Journal of Antibiotics,2016,vol. 69,p. 368 - 380
[2]Patent: EP1970377,2008,A1 .Location in patent: Page/Page column 67

7
[ 21462-39-5 ]
[ 1446499-23-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625

8
[ 21462-39-5 ]
C₃₇H₆₂N₄O₁₂S₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625

9
[ 21462-39-5 ]
[ 1446499-12-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625

10
[ 21462-39-5 ]
[ 1446499-13-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625

11
[ 21462-39-5 ]
[ 2150-02-9 ]
[ 1446499-12-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625

12
[ 108-24-7 ]
[ 21462-39-5 ]
[ 2150-02-9 ]
[ 1446499-11-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5613 - 5625

13
[ 693-38-9 ]
[ 21462-39-5 ]
clindamycin palmitate [ No CAS ]