Ammonium Chloride → HCID 86618213, compound

HRID 1669523Notes

Reaction equation

HRID 1669523 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]([CH2:24][N:25]([O:29]C(=O)C)[C:26](=[O:28])[CH3:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[NH4+].[Cl-]>CO>[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]([CH2:24][N:25]([C:26](=[O:28])[CH3:27])[OH:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 86618212HCID 86618212, compound

Product 1

HCID 86618213HCID 86618213, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {(S)-1-[(Acetoxy-acetyl-amino)-methyl]-2-[4-(4-chloro-phenoxy)-phenyl]-ethyl}-carbamic acid tert butyl ester (27 mg, 0.057 mmol, 1 eq.) in MeOH (2 ml) was added sodium methoxide (15 mg, 0.27 mmol, 4.7 eq.) until pH=10. The mixture was stirred at room temperature for 30 min. Then was poured into saturated NH4Cl solution (15 ml). The mixture was extracted with dichloromethane (3×5 ml). The combined DCM layers were washed with sodium bicarbonate solution (5 ml) and dried over anhydrous MgSO4. Removal of solvent under reduced pressure gave the desired product (20 mg, 81% yield) as an oil.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×5 ml)
  2. washThe combined DCM layers were washed with sodium bicarbonate solution (5 ml)
  3. dry with materialdried over anhydrous MgSO4
  4. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-66921af6bb01433d92e5afeb980e09a3
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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