Sodium Acetate → HCID 13749511, compound

HRID 1249276Notes

Reaction equation

HRID 1249276 reaction equation
C([BH3-])#N.[Na+].O=[C:6]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:22]([O:29][C:30]([CH:32]([N:34]1[CH2:40][CH2:39][CH2:38][CH2:37][C@H:36]([NH:41]C(C(OCC)=O)CCC2C=CC=CC=2)[C:35]1=[O:56])[CH3:33])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[Na+]>C(O)C>[CH2:22]([O:29][C:30]([CH:32]([N:34]1[CH2:40][CH2:39][CH2:38][CH2:37][C@H:36]([NH:41][CH:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:35]1=[O:56])[CH3:33])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 13749503HCID 13749503, compoundHCID 14187456HCID 14187456, compound

Product 1

HCID 13749511HCID 13749511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 490 mg sodium cyanoborohydride in 3 ml ethanol is added over 2.5 hrs to a solution of 2.43 g t-butyl 2-oxo-4-phenylbutyrate, 850 mg 1-(1-benzyloxycarbonylethyl)-3-(S)-aminoperhydroazepin-2-one hydrochloride (from Isomer A, Example 24) and 267 mg sodium acetate in 10 ml ethanol. The reaction is stirred at room temperature overnight, filtered and concentrated. The residue is partitioned between ethyl acetate and 5% sodium bicarbonate. After drying, concentration of the organic phase affords a residue which is chromatographed over silica gel with hexane-ethyl acetate (7:3) giving the pure diastereomers of 1-(1-benzyloxycarbonylethyl)-3-(S)-(1-t-butoxycarbonyl-3-phenylpropyl)aminoperhydroazepin-2-one.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue is partitioned between ethyl acetate and 5% sodium bicarbonate
  4. customAfter drying
  5. customconcentration of the organic phase affords a residue which
  6. customis chromatographed over silica gel with hexane-ethyl acetate (7:3)

Sources & evidence

ORD record
ord-c033f0e6dd944080aa3fd5de02e5805e
Source dataset
uspto-grants-1986_12
Patent number
US04629787

Reaction notes

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