Trifluoroacetic acid → HCID 68158718, compound

HRID 1524648Notes

Reaction equation

HRID 1524648 reaction equation
C(OC(=O)[NH:7][C@:8]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[C@H:12]([CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[C@@H:11]([CH3:19])[O:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@:8]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[CH2:9][O:10][C@H:11]([CH3:19])[C@H:12]1[CH:13]([OH:18])[C:14]([F:17])([F:15])[F:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86668887HCID 86668887, compound

Product 1

HCID 68158718HCID 68158718, compoundYield 1,334.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(3S,4R,5R)-3-(2-Fluoro-phenyl)-5-methyl-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester (Preparation Example 30-(3)) (1.20 g, 0.23 mmol) was dissolved in DCM (20 ml). TFA (10 ml) was added. The reaction mixture was stirred overnight (16 h). The reaction was then concentrated, 10 ml of aqueous saturated sodium carbonate was added then extracted with DCM (2×40 ml). 900 mg (86%) of a mixture of the title compound (85%) and its epimer at the CF3 position (15%) were isolated.

Workup

  1. concentrationThe reaction was then concentrated
  2. addition10 ml of aqueous saturated sodium carbonate was added
  3. extractionthen extracted with DCM (2×40 ml)

Sources & evidence

ORD record
ord-d479da0886744af08b1c53cac33a9169
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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