Trifluoroacetic acid → HCID 131734577, compound

HRID 595249Notes

Reaction equation

HRID 595249 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][CH2:9][CH:10]([OH:21])[C@H:11]([NH:13]C(=O)OC(C)(C)C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[Cl:8][CH2:9][C@H:10]([OH:21])[CH2:11][NH3+:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734576HCID 131734576, compound

Product 1

HCID 131734577HCID 131734577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.70 mL, 9.0 mmol) was added to a mixture of tert-butyl ((2R)-4-chloro-3-hydroxybutan-2-yl)carbamate (200 mg, 0.89 mmol) in dichloromethane (1.4 mL) and the mixture was stirred for one hour. The mixture was concentrated to afford (R)-3-chloro-2-hydroxypropan-1-aminium 2,2,2-trifluoroacetate. 1H NMR (500 MHz, DMSO-d6) δ 7.80 (s, 3H), 3.84 (td, J=6.8, 3.2 Hz, 1H), 3.76-3.63 (m, 1H), 3.61 (dd, J=11.3, 6.0 Hz, 1H), 3.51 (dd, J=11.2, 7.1 Hz, 1H), 3.39-3.30 (m, 1H), 1.08 (d, J=6.8 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4d4c2d4d7d9644ed98ffed5a9209a668
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

Loading…