Trifluoroacetic acid → HCID 69410367, compound

HRID 1182086Notes

Reaction equation

HRID 1182086 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:24](C1C=CC=CC=1)(C1C=CC=CC=1)[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12]1)(C)(C)C.F[C:45](F)(F)[C:46](O)=O>ClCCl>[NH2:7][C@H:8]([CH2:24][O:25][Si:26]([C:27]([CH3:28])([CH3:30])[CH3:29])([C:46]1[CH:45]=[CH:10][CH:9]=[CH:8][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([C:15]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[O:23])[CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726650HCID 131726650, compound

Product 1

HCID 69410367HCID 69410367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of {(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-[3-(4-fluoro-benzoyl)-azetidin-1-yl]-propyl}-carbamic acid tert-butyl ester. (0.188 g, 0.321 mmol) in dichloromethane (5 ml) is treated with trifluoroacetic acid, and stirred at ambient temperature for 0.5 hour. The reaction mixture is diluted with dichloromethane and washed with water and saturated aqueous NaHCO3. The organic phase is dried over MgSO4 and evaporated to afford {1-[(S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-butyl]-azetidin-3-yl)-(4-fluoro-phenyl)-methanone. [MH]+ 505.2.

Workup

  1. washwashed with water and saturated aqueous NaHCO3
  2. dry with materialThe organic phase is dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-1d50eddfd3674f02b1982a5b6a05326e
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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