Chloroform → HCID 86593963, compound

HRID 1611653Notes

Reaction equation

HRID 1611653 reaction equation
[C:1]([NH:6][C@H:7]([C:29]([NH:31][CH2:32][CH2:33][S:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[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>CCCCCC>[C:1]([NH:6][C@H:7]([C:29]([NH:31][CH2:32][CH2:33][S:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:30])[CH2:8][SH:9])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 484333Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)esterHCID 21881112Ethyl ether methylene chlorideHCID 56984260HCID 56984260, compound

Product 1

HCID 86593963HCID 86593963, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

This compound is obtained by the S-detritylation of 17 (2.68 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 25%). I-219 is isolated in the form of a gum which, after trituration in hexane, provides a colorless powder (Yd=58%). Rf (CH2Cl2/ether, 6/4): 0.35. M.p.=127-130° C. [α]D20=−20.8° (c 1.06, 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 25%)
  3. customI-219 is isolated in the form of a gum which

Sources & evidence

ORD record
ord-7baeafe59dbb47ba81ed99d160057082
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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