Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)ester → HCID 516557, compound

HRID 1611647Notes

Reaction equation

HRID 1611647 reaction equation
[C:1]([NH:4][C@H:5]([C:27]([NH:29][CH2:30][CH2:31][S:32][C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:28])[CH2:6][S:7]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:3])[CH3:2].C(N[C@H](C(NCCSC(=O)C)=O)CS)(=O)C.C(Cl)Cl.CO>C(Cl)(Cl)Cl>[C:1]([NH:4][C@H:5]([C:27]([NH:29][CH2:30][CH2:31][S:32][C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:28])[CH2:6][SH:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 484333Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)esterHCID 11284496HCID 11284496, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 516557HCID 516557, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This compound is obtained by the S-detritylation of 12 (4.44 mmol). The protocol used is the same as that described in example 1 for the synthesis of I-152. After the various treatments, a gum is collected, which gum is purified by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 50%). I-198 is isolated in the form of a white solid with a yield of 63%. Rf CH2Cl2/MeOH, 9.5/0.5): 0.38. M.p.=128-130° C. [α]D20=−24.7° (c 1.01, CHCl3).

Workup

  1. customAfter the various treatments, a gum is collected
  2. customwhich gum is purified by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 50%)
  3. customI-198 is isolated in the form of a white solid with a yield of 63%

Sources & evidence

ORD record
ord-33a190a09bf4445ab9c2db3f7791387b
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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