Ammonia → HCID 58941324, compound

HRID 747633Notes

Reaction equation

HRID 747633 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:10][C:11](O)=[O:12])=[C:4]([CH2:27][C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=2[F:35])[CH:3]=1.C([N:38]1CCOCC1)C.ClC(OCC)=O.N>O1CCCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:10][C:11]([NH2:38])=[O:12])=[C:4]([CH2:27][C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=2[F:35])[CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 7525EthylmorpholineHCID 10928Ethyl chloroformateHCID 69223884HCID 69223884, compound

Product 1

HCID 58941324HCID 58941324, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 0.8 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-N-[(3,4-dimethoxyphenyl)sulfonyl]-β-alanine dissolved in 16 ml of tetrahydrofuran are added, at 0° C., 0.21 ml of N-ethylmorpholine and 0.16 ml of ethyl chloroformate. The mixture is left at room temperature for 1 hour, and 1.36 ml of ammonia (20%) in water are then introduced. After 48 hours at room temperature, the reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated, and the residue is chromatographed on a column of silica gel, eluting with a 98/2 (v/v) dichloromethane/methanol mixture to give 0.295 g of the expected product.

Workup

  1. additionare added, at 0° C.
  2. waitAfter 48 hours at room temperature
  3. washwashed with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is chromatographed on a column of silica gel
  7. washeluting with a 98/2 (v/v) dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-f641ed2081dd4a3ebc5e06140f7b97aa
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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