NADP nicotinamide-adenine-dinucleotide phosphate → 1,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	NADP nicotinamide-adenine-dinucleotide phosphate	HCID 5886	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal	HCID 107526	—
Reactant	tert-butyl N-((2S)-4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate	HCID 9926241	—
Solvent	Toluene	HCID 1140	—
Product	1,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate	HCID 9944139	99.1%

Reaction Conditions

Temperature	30 °C

Reaction Steps

Glucose 3 g, NADP 3 mg, toluene 0.25 ml, and (3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 2.5 g were added to 25 ml of a cultured medium of E. coli HB101 (pNTOM4G1) prepared in the same manner as in Example 7, and the mixture was stirred at 30° C. for 40 hr while adjusting to pH 6.5 by dropwise addition of 5 M sodium hydroxide. After completion of the reaction, the reaction mixture was extracted with toluene, desolvated and the extract was analyzed in the same manner as in Example 8. As a result, (2R,3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanol (yield 99.1%, diastereomeric excess 99.8% d.e.) was obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915022B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-14917c0b9c18414e887758d9d7f091a4
Source note	uspto-grants-2011_03