Chloroform → HCID 57324803, compound

HRID 489883Notes

Reaction equation

HRID 489883 reaction equation
[C:1]([NH:6][C@H:7]([C:29]([NH:31][CH2:32][CH2:33][S:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[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:40])[C:36]([CH3:37])([CH3:39])[CH3:38])=[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 86593962HCID 86593962, compound

Product 1

HCID 57324803HCID 57324803, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

This compound is obtained by the S-detritylation of 16 (2.78 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 22%). I-214 is isolated in the form of a gum which, after trituration in hexane, provides a colorless powder (Yd=70%). Rf (CH2Cl2/ether, 5/5): 0.46. M.p.=120-122° C. [α]D20=−25° (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 22%)
  3. customI-214 is isolated in the form of a gum which

Sources & evidence

ORD record
ord-a4ffb2755603478c96b5a76c2bc1cc58
Source dataset
uspto-grants-2005_12
Patent number
US06979747B2

Reaction notes

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