Trifluoroacetic acid → HCID 70073493, compound

HRID 2269363Notes

Reaction equation

HRID 2269363 reaction equation
[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][C:7](=[O:32])[C@@H:8]([NH:24]C(OC(C)(C)C)=O)[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].FC(F)(F)C(O)=O>ClCCl>[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][C:7](=[O:32])[C@@H:8]([NH2:24])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70085747HCID 70085747, compound

Product 1

HCID 70073493HCID 70073493, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylaminohexanoic acid 1,3,4-thiadiazol-2-ylamide (0.81 g, 1.75 mmol) in dichloromethane (8 mL) is added trifluoroacetic acid (2 mL). The resulting solution is stirred for 4 h at 25° C., is concentrated, diluted with 50 mL of EtOAc, and washed with 1 N aqueous sodium hydroxide solution. The organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide (2S)-6-benzyloxycarbonylamino-2-aminohexanoic acid 1,3,4-thiadiazol-2-ylamide as a solid (0.62 g, 98% yield).

Workup

  1. concentrationis concentrated
  2. additiondiluted with 50 mL of EtOAc
  3. washwashed with 1 N aqueous sodium hydroxide solution
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5075a3c8fd3469483865e63ff6306e2
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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