Trifluoroacetic acid methylene chloride → HCID 131712071, compound

HRID 1390153Notes

Reaction equation

HRID 1390153 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:34]([C:39]([OH:41])=[O:40])[CH2:35][CH2:36][S:37][CH3:38])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:49][CH:50]([CH2:53][OH:54])[CH2:51][OH:52].[C:55](O)([C:57]([F:60])([F:59])[F:58])=[O:56].C(Cl)Cl>>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:34]([C:39]([OH:41])=[O:40])[CH2:35][CH2:36][S:37][CH3:38])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1.[F:58][C:57]([F:60])([F:59])[C:55]([O:52][CH2:51][C@@H:50]([CH2:53][OH:54])[NH2:49])=[O:56]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 131712072HCID 131712072, compound

Product 1

HCID 131712071HCID 131712071, compound

Procedure

2 g of Boc-Tyr-(D)-Ala-Gly-Phe-Met-serinol are dissolved at room temperature in 10 ml of CF3COOH/CH2Cl2 (1:1 v/v). After 30 minutes, the mixture is concentrated under vacuum and the residue triturated with ether. The solid product is recrystallized from methanol/ether to yield the title compound. M.P. 200° (decomp.). [α]D20 =+2.1° (C=1.0 in DMF).

Workup

  1. concentrationthe mixture is concentrated under vacuum
  2. customthe residue triturated with ether
  3. customThe solid product is recrystallized from methanol/ether

Sources & evidence

ORD record
ord-b64466fb662a49a9a4de17bbc48f8f1d
Source dataset
uspto-grants-1981_01
Patent number
US04247543

Reaction notes

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