Hydrochloric Acid → HCID 70153857, compound

HRID 1017985Notes

Reaction equation

HRID 1017985 reaction equation
C[O:2][C:3](=[O:44])[CH2:4][C@@H:5]([NH:35][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[O:24])=[C:18]([O:33][CH3:34])[CH:17]=2)[C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO>[C:36]([NH:35][C@@H:5]([C:6]1[CH:7]=[CH:8][C:9]([N:12]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[O:24])=[C:18]([O:33][CH3:34])[CH:17]=2)[C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=1)[CH2:4][C:3]([OH:44])=[O:2])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70152433HCID 70152433, compound

Product 1

HCID 70153857HCID 70153857, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (R)-3-benzoylamino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenyl-acetylamino}phenyl)-propanoic acid methyl ester [4.08 g, Reference Example 12(a)], and methanol (40 ml) was heated to 40° C. and then treated with 10% aqueous sodium hydroxide solution (34 ml). After stirring at 40° C. for 2.5 hours, the reaction mixture was cooled and then acidified to pH 1.0 by addition of hydrochloric acid (1M). The resultant white solid was collected, washed with water and then dried in vacuo. Recrystallisation from acetic acid gave the title compound as a white crystalline solid (3.2 g), m.p. 220-222° C. MS: MH+ 581. [Elemental analysis:—C, 68.0; H, 5.4; N, 9.5%. Calculated for C33H32N4O6:—C, 68.3; H, 5.6; N, 9.65%]. 99% ee by HPLC analysis on a CHIRALPAK AD F294 column eluting with heptane:isopropanol:ethanol:trifluoroacetic acid (200:25:25:1) at a rate of 0.7 ml/min.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe resultant white solid was collected
  3. washwashed with water
  4. customdried in vacuo
  5. customRecrystallisation from acetic acid

Sources & evidence

ORD record
ord-bbddb5b8935b40f2adc8873bf25598d3
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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