Water → HCID 86708073, compound

HRID 1524368Notes

Reaction equation

HRID 1524368 reaction equation
[C:1]([O:5][C:6]([N:8]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:9]([CH2:15][C:16]([F:23])([F:22])/[CH:17]=[CH:18]/[N+:19]([O-:21])=[O:20])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.OP([O-])(O)=O.[K+]>C1COCC1>[C:27]([O:26][C:24]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C@H:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:15][C:16]([F:23])([F:22])[CH2:17][CH2:18][N+:19]([O-:21])=[O:20])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 516951Monobasic potassium phosphateHCID 4311764Sodium borohydrideHCID 86708074HCID 86708074, compound

Product 1

HCID 86708073HCID 86708073, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S,5E)-2-[bis(tert-butoxycarbonyl)amino]-4,4-difluoro-6-nitrohex-5-enoate, from Step 4 (2.81 g, 6.40 mmol) in THF (64 mL) at 6° C. was added sodium borohydride (1.212 g, 32.0 mmol) followed by a slow addition of water (12.8 mL). The reaction mixture was stirred at room temperature for 4 hours, poured into 10% KH2PO4, and extracted with EtOAc (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 2.725 g of the title compound (colorless oil) that was used without further purification.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-016cd221f1374275b39c47c51fcefdd1
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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