Water → HCID 68425957, compound

HRID 1785614Notes

Reaction equation

HRID 1785614 reaction equation
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[O:4].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[O:31])=[CH:25][CH:24]=1.O>CN(C)C=O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C@@H:2]([NH:1][C:30](=[O:31])[CH2:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[C:3]([NH2:5])=[O:4])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 45158935(2R)-2-Amino-2-(4-methoxyphenyl)acetamide

Product 1

HCID 68425957HCID 68425957, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-2-amino-2-(4-methoxyphenyl)acetamide (200 g, 1.11 mol), triethylamine (124 g, 1.22 mol) in dimethylformamide (2 L) is cooled to 5° C. in an ice bath and (4-methoxyphenyl)acetyl chloride (225 g, 187 mL, 1.22 mol) is added dropwise at a rate which maintains the temperature in a range from 5° C. to 7° C. After 1.5 hours the additional stirring in the cold, the reaction solution is transferred to a vessel containing water (12 L). The solid which forms upon standing is collected and rinsed several times with water. The material collected is dried to a constant weight affording 323.9 g (89% yield) of the desired product. Analysis by chiral HPLC indicates 98.6% enantiomeric purity.

Workup

  1. customfrom 5° C. to 7° C
  2. customis transferred to a vessel
  3. customupon standing is collected
  4. washrinsed several times with water
  5. customThe material collected
  6. customis dried to a constant weight

Sources & evidence

ORD record
ord-cd20c2f31fb0433fb0efbb3a90109058
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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