Trifluoroacetic acid → ((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester trifluoroacetate

HRID 418350Notes

Reaction equation

HRID 418350 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C:11]1[S:12][C:13]2[CH2:19][C@@H:18]([NH:20]C(OC(C)(C)C)=O)[CH2:17][CH2:16][C:14]=2[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>C(Cl)Cl>[F:32][C:31]([F:34])([F:33])[C:29]([OH:35])=[O:30].[CH2:1]([O:8][C:9](=[O:28])[NH:10][C:11]1[S:12][C:13]2[CH2:19][C@@H:18]([NH2:20])[CH2:17][CH2:16][C:14]=2[N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59190873((S)-6-tert-butoxycarbonylamino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester

Product 1

HCID 86761484((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved ((S)-6-tert-butoxycarbonylamino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester in 20 mL of CH2Cl2. Added 20 mL of TFA. Stirred for 1 h. LC-MS analysis indicated complete deprotection of BOC group. Concentrated to give 46.0 g of ((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester trifluoroacetate as pale yellow solid.

Workup

  1. concentrationConcentrated

Sources & evidence

ORD record
ord-4256ec0fd27041d69ff4bd6d6f593a98
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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