Dimethylformamide → HCID 57071264, compound

HRID 1166143Notes

Reaction equation

HRID 1166143 reaction equation
C[N:2](C)C=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:15](=[O:22])[C@@H:14]([CH2:23][C:24]([OH:26])=O)[O:13][C@H:12]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=3[O:35][CH3:36])[C:11]=2[CH:37]=1.[Cl-].[NH4+].C(OP(C#N)(=O)OCC)C>C(N(CC)CC)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]([CH2:17][C:18]([CH3:19])([CH3:21])[CH3:20])[C:15](=[O:22])[C@@H:14]([CH2:23][C:24]([NH2:2])=[O:26])[O:13][C@H:12]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=3[O:35][CH3:36])[C:11]=2[CH:37]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 76257Diethyl cyanophosphonateHCID 9847159HCID 9847159, compound

Product 1

HCID 57071264HCID 57071264, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

A dimethylformamide solution of (3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-neopentyl-2-oxo-1,2, 3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (2.0 g), ammonium chloride (1.2 g) and triethylamine (1.0 ml) was cooled in ice bath. To the solution were added diethylcyanophosphonate (0.85 g) and triethylamine (0.5 ml). The mixture was stirred for further 20 minutes, to which was added ice-water, followed by extraction with ethyl acetate. The organic layer was washed with water, which was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from diethyl ether to give 1.0 g of (3R,5S)-7-chloro-5-(2, 3-dimethoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetamide as colorless crystals, m.p. 170-172° C.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-b9e1658d918045d39d948fb7107a6304
Source dataset
uspto-grants-2003_09
Patent number
US06613761B1

Reaction notes

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