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

HRID 1712874
Notes
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Reaction equation

HRID 1712874 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 9926241tert-butyl N-((2S)-4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate2×

Product 1

HCID 99441391,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate
Yield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

  1. custom(pNTOM5G1) prepared in the same manner as in Example 7
  2. additionwas added
  3. customthe mixture was reacted for 20 hr
  4. customAfter completion of the reaction
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes