Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)ester → HCID 86593958, compound

HRID 1611650Notes

Reaction equation

HRID 1611650 reaction equation
[C:1]([NH:6][C@H:7]([C:29]([NH:31][CH2:32][CH2:33][S:34][C:35](=[O:37])[CH3:36])=[O:30])[CH2:8][S:9]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(N[C@H](C(NCCSC(=O)C)=O)CS)(=O)C.C(Cl)Cl.CCOCC>C(Cl)(Cl)Cl>[C:1]([NH:6][C@H:7]([C:29]([NH:31][CH2:32][CH2:33][S:34][C:35](=[O:37])[CH3:36])=[O:30])[CH2:8][SH:9])(=[O:5])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 484333Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)esterHCID 21881112Ethyl ether methylene chlorideHCID 87919653HCID 87919653, compound

Product 1

HCID 86593958HCID 86593958, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This compound is obtained by the S-detritylation of 14 (2.56 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: CH2Cl2/ether 30%). I-203 is isolated in the form of white solid with a yield of 70%. Rf CH2Cl2/ether, 5/5): 0.44. M.p.=117-120° C. [α]D20=−36.5° (c 1.04, 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: CH2Cl2/ether 30%)
  3. customI-203 is isolated in the form of white solid with a yield of 70%

Sources & evidence

ORD record
ord-c9c248a443864a9cb52c0759026c5ff3
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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