Triethylamine → 137431-02-8

HRID 2379192Notes

Reaction equation

HRID 2379192 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[F:17])[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:5].CNC(N1C[C@H](P(C2CCCCC2)C2CCCCC2)C[C@@H]1CP(C1C=CC=CC=1)C1C=CC=CC=1)=O.C(N(CC)CC)C.[H][H]>CO>[NH2:2][CH2:3][C@@H:4]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[F:17])[NH:9][S:10]([CH3:13])(=[O:11])=[O:12])[OH:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11731056HCID 11731056, compoundHCID 18958065HCID 18958065, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9838763137431-02-8Yield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3'-(2-Aminoacetyl)-4'-fluoromethanesulfonanilide hydrochloride (21 g) was suspended in 210 ml of methanol, then a catalyst prepared from 50 mg of (2R,4R)-N-methylcarbamoyl-4-dicyclohexylphosphino-2-diphenylphosphinomethylpyrrolidine and 18 mg of di-μ-chlorobis(cyclooctadiene)dirhodium (I) was added thereto together with 19 mg of triethylamine and the mixture was reduced at 50° C. in an atmosphere of hydrogen of 20 atm. The reaction mixture was concentrated and made into a free base using ion exchange resin (Dowex 50W X2) to give 15.8 g of crude (R)-(-)-3'-(2-amino-1-hydroxyethyl)-4'-fluoromethanesulfonanilide.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4e75c1f88fe445979782a25673c8a2ba
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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