Sodium Hydroxide → HCID 9960383, compound

HRID 1266453Notes

Reaction equation

HRID 1266453 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:39])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[O:28])=[C:22]([O:37][CH3:38])[CH:21]=3)=[CH:13][CH:12]=2)[CH2:9][N:8]([C:40](=[O:48])[CH2:41][CH2:42][C:43]([O:45]CC)=[O:44])[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:43]([CH2:42][CH2:41][C:40]([N:8]1[CH2:9][CH:10]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:39])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[O:28])=[C:22]([O:37][CH3:38])[CH:21]=3)=[CH:13][CH:12]=2)[CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:48])([OH:45])=[O:44]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54146001HCID 54146001, compound

Product 1

HCID 9960383HCID 9960383, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A stirred solution of 1-(3-ethoxycarbonyl-propionyl)4-(4-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (0.3 g, Reference Example 10) in ethanol (3 ml) was treated dropwise with aqueous sodium hydroxide solution (1.8 ml and then 0.9 ml after 20 hours, 1N). After stirring at 20° C. for a further 2 hours the mixture was evaporated (40° C. and 2.7 kPa). The residue was treated with water (50 ml), then cooled to 5° C. and the pH of the mixture adjusted to 2 by dropwise addition of hydrochloric acid (10 ml, 1 N). The aqueous solution was triturated with ethyl acetate (50 ml), affording the title compound (130 mg) as a white solid, m.p. 184° C. TLC: RF=0.5 (on silica eluting with a mixture of dichloromethane and methanol, 50:50).

Workup

  1. customwas evaporated (40° C. and 2.7 kPa)
  2. additionThe residue was treated with water (50 ml)
  3. temperaturecooled to 5° C.
  4. additionthe pH of the mixture adjusted to 2 by dropwise addition of hydrochloric acid (10 ml, 1 N)
  5. customThe aqueous solution was triturated with ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-11ea79170a06489c9c35eac838adf121
Source dataset
uspto-grants-2003_04
Patent number
US06548533B2

Reaction notes

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