Water → HCID 69034930, compound

HRID 2415454Notes

Reaction equation

HRID 2415454 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([I:18])=[C:12]([CH2:14][C:15]([OH:17])=O)[CH:13]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:23]1[CH:27]=[CH:26]N=C1)=O.O.C[N:35]([CH:37]=[O:38])C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([I:18])=[C:12]([CH2:14][C:15]([NH:23][C@@H:27]([CH3:26])[C:37]([NH2:35])=[O:38])=[O:17])[CH:13]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 22641948HCID 22641948, compound

Product 1

HCID 69034930HCID 69034930, compound

Conditions

Temperature
50 °C

Procedure

A mixture of (5-(4-fluoro-benzyloxy)-2-iodo-phenyl]-acetic acid (example 45a, 355 mg, 0.919 mmol) and 1,1′-carbonyl-diimidazole (164 mg, 1.01 mmol) in N,N′-dimethylformamide (2 mL) was stirred at 50° C. for 1.5 h. H-L-alanine-NH2HCl (145 mg, 1.16 mmol) was added and the mixture was stirred at 50° C. overnight. Water was added and the product precipitated. The solid was filtrated (368 mg, 88%). MS: m/e=457.2 (M+H+).

Workup

  1. additionH-L-alanine-NH2HCl (145 mg, 1.16 mmol) was added
  2. stirringthe mixture was stirred at 50° C. overnight
  3. customthe product precipitated
  4. filtrationThe solid was filtrated (368 mg, 88%)

Sources & evidence

ORD record
ord-5a733b43e5df4424b04d09d966dc349a
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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