Diethyl Ether → H-Thr-Cys(MBzl)-Thr-ol trifluoroacetate

HRID 1903337Notes

Reaction equation

[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[NH:8](C(OC(C)(C)C)=O)[C@H:9]([C:13]([NH:15][C@H:16]([C:27]([NH:29][C@H:30]([CH2:34][OH:35])[C@@H:31]([CH3:33])[OH:32])=[O:28])[CH2:17][S:18][CH2:19][C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)=[O:14])[C@@H:10]([CH3:12])[OH:11].C1(SC)C=CC=CC=1.C(OCC)C>C(Cl)Cl>[NH2:8][C@H:9]([C:13]([NH:15][C@H:16]([C:27]([NH:29][C@H:30]([CH2:34][OH:35])[C@@H:31]([CH3:33])[OH:32])=[O:28])[CH2:17][S:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=1)=[O:14])[C@@H:10]([CH3:12])[OH:11].[F:4][C:3]([C:1]([OH:7])=[O:2])([F:6])[F:5]

Participants

Conditions

Temperature: 0 °C

Procedure

150 ml TFA are added to a solution of 16 g BOC-Thr-Cys(MBzl)-Thr-ol and 17 ml thioanisole in 100 ml methylene chloride pre-cooled to 0° C. The whole is allowed to stand for 20 minutes at room temperature and stirred into ethyl-ether. The precipitated product is filtered off, washed with ethyl-ether and dried to yield the title compound:

Workup

filtrationThe precipitated product is filtered off
washwashed with ethyl-ether
customdried

Sources & evidence

ORD record: ord-e03e2c08e50b4b4ab4e548ebc7a0bd5d
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04435385

Reaction notes

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