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

HRID 1712874Notes

Reaction equation

O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.[Cl:61][CH2:62][C:63](=[O:80])[C@@H:64]([NH:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:61][CH2:62][C@H:63]([OH:80])[C@@H:64]([NH:72][C:73]([O:75][C:76]([CH3:78])([CH3:77])[CH3:79])=[O:74])[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Glucose 6 g, NADP 1.4 mg, toluene 0.25 ml, and (3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 2.5 g were added to 50 ml of a cultured medium of E. coli HB101 (pNTOM5G1) prepared in the same manner as in Example 7, and the mixture was stirred at 30° C. while adjusting to pH 6.5 by dropwise addition of 5 M sodium hydroxide. One hour after the start of the reaction, 2.5 g of (3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone was added, and the mixture was reacted for 20 hr. 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 99.6%, diastereomeric excess 99.8% d.e.) was obtained.

Workup

custom(pNTOM5G1) prepared in the same manner as in Example 7
additionwas added
customthe mixture was reacted for 20 hr
customAfter completion of the reaction
extractionthe reaction mixture was extracted with toluene

Sources & evidence

ORD record: ord-40eb88d1edaa4f0f8201e7f35c77a3f3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07794993B2

Reaction notes

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