Sodium Hydroxide → HCID 44461524, compound

HRID 393432Notes

Reaction equation

HRID 393432 reaction equation
C[O:2][C:3](=[O:41])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])=[O:32])=[CH:26][CH:25]=1)[NH:5][C:6]([C:8]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[OH-].[Na+]>C(O)C>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[C:31]([NH:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][C@@H:4]([C:3]([OH:41])=[O:2])[NH:5][C:6]([C:8]2([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:7])=[CH:29][CH:28]=1)=[O:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23383926HCID 23383926, compound

Product 1

HCID 44461524HCID 44461524, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(4-methoxyphenyl-methyl)cyclohexy]carbonyl]-L-phenylalanine methyl ester (0.15 g, 0.25 mmol) in ethanol (2 mL) was added aqueous 1.0 N sodium hydroxide (1.5 mL, 3 mmol) at room temperature. The mixture was heated to 50° C. and the resulting clear solution was stirred overnight. The mixture was concentrated, the residue was diluted with 5 mL of water and extracted with 25 mL of ether to remove any neutral impurities. The aqueous layer was acidified with 1 N HCl and the precipitated white solid was collected by filtration and washed with water (20 mL) and hexane (20 mL). After air-drying, 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(4-methoxyphenylmethyl)cyclohexyl]carbonyl]-L-phenylalanine (0.12 g, 82%) was obtained as a white solid, mp 136-140° C. HR MS: Obs mass, 583.1763. Calcd mass, 583.1766 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with 5 mL of water
  3. extractionextracted with 25 mL of ether
  4. customto remove any neutral impurities
  5. filtrationthe precipitated white solid was collected by filtration
  6. washwashed with water (20 mL) and hexane (20 mL)
  7. customAfter air-drying

Sources & evidence

ORD record
ord-96d58f1482d345698f3776855311a0e5
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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