Trifluoroacetic acid → H-Cys(MBzl)-Thr-ol trifluoroacetate

HRID 1903335Notes

Reaction equation

HRID 1903335 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([CH2:20][OH:21])[C@@H:17]([CH3:19])[OH:18])=[O:14])[CH2:3][S:4][CH2:5][C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1.C1(SC)C=CC=CC=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl.C(OCC)C>[NH2:1][C@H:2]([C:13]([NH:15][C@H:16]([CH2:20][OH:21])[C@@H:17]([CH3:19])[OH:18])=[O:14])[CH2:3][S:4][CH2:5][C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1.[F:40][C:39]([C:37]([OH:43])=[O:38])([F:42])[F:41]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 131713414BOC-Cys(MBzl)-Thr-ol

Product 1

HCID 131713415H-Cys(MBzl)-Thr-ol trifluoroacetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

7.1 g BOC-Cys(MBzl)-Thr-ol and 5 ml thioanisole are dissolved in 25 ml methylene chloride. The solution is added to 50 ml TFA and allowed to stand for 20 minutes at room temperature. The mixture is diluted with ca. 1.5 liters ethyl-ether and the precipitated product filtered off and dried to yield the title compound:

Workup

  1. filtrationthe precipitated product filtered off
  2. customdried

Sources & evidence

ORD record
ord-bc77261974d2451e85c3866ef5f256dc
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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