Trifluoroacetic acid → HCID 57222681, compound
Reaction equation
[CH2:1]([C@H:8]([NH:19]C(=O)OC(C)(C)C)[C@H:9]([OH:18])[CH2:10][NH:11][O:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:19][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]([OH:18])[CH2:10][NH:11][O:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15]Participants
Procedure
A mixture of tert-butyl (1S,2R)-1-benzyl-3-[(1-ethylpropoxy)amino]-2-hydroxypropylcarbamate (3.285 g, 8.98 mmol) and trifluoroacetic acid (25 mL) was stirred at ambient temperature under Argon for approximately 30 minutes. The reaction was evaporated in vacuo and the residue was partitioned between dichloromethane and aqueous sodium hydroxide (1N). The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filter, evaporated in vacuo and dried under high vacuum to provide (2R,3S)-3-amino-1-[(1-ethylpropoxy)amino]-4-phenyl-2-butanol (2.455 g, 100%) as a solid. H1-NMR (chloroform-D3): 0.94 (m, 6H), 1.56 (m, 4H), 2.55 (m, 1H), 3.01 (m, 2H), 3.22 (m, 2H), 3.51 (m, 1H), 3.81 (m, 1H), 7.30 (m, 5H). MS(ESI): 267(M+H).
Workup
- customThe reaction was evaporated in vacuo
- customthe residue was partitioned between dichloromethane and aqueous sodium hydroxide (1N)
- customThe phases were separated
- extractionthe aqueous phase was extracted with dichloromethane
- dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
- filtrationfilter
- customevaporated in vacuo
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-c8b61e4b77d4410f9340b37d94387c8a
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07419967B2
Reaction notes
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