Water → HCID 53905992, compound

HRID 274811Notes

Reaction equation

HRID 274811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH:12]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:13]([NH:20][C:21]([NH:23][C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27]([O-:29])=[O:28])=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])=[CH:4][CH:3]=1.O.[OH-].[Li+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:11][CH:12]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:13]([NH:20][C:21]([NH:23][C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27]([OH:29])=[O:28])=[O:22])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 131718857HCID 131718857, compound

Product 1

HCID 53905992HCID 53905992, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl-(-)-[S-(R*,R*)]-3-[[[[2-[[[(4-chlorophenyl)amino]carbonyl]amino]-1,2-diphenylethyl]amino]carbonyl]amino]benzoate (0.15 g, 0.27 mmol) in MeOH (8 mL) is added lithium hydroxide monohydrate (0.01 g, 0.27 mmol) followed by water to the cloud point. The resulting mixture is stirred overnight at room temperature. The mixture is warmed to 50° C. for 3 hours. The solvent is removed in vacuo and the residue partitioned between water and diethyl ether. The layers are separated and the aqueous layer is acidified to pH=2 with 2 M HCl. The resulting solid is filtered and dried in vacuo at 114° C. for 5 hours, mp 172.5°-173° C. IR (KBr): 3383, 1662, 1550, 1493, 1234, 698 cm-1. NMR (DMSO-d6): δ5.02 (m, 2H), 6.95-7.53 (m, 19H), 8.06 (s, 1H), 8.80 (s, 1H), 8.88 (s, 1H), 12.83 (br s, 1H). Analysis calculated for C29H25ClN4O4.0.5H2O: C, 64.74; H, 4.87; N, 10.41. Found: C, 64.57; H, 4.83; N, 10.10. [α]D25 =-22.3° (c=1, DMF).

Workup

  1. temperatureThe mixture is warmed to 50° C. for 3 hours
  2. customThe solvent is removed in vacuo
  3. customthe residue partitioned between water and diethyl ether
  4. customThe layers are separated
  5. filtrationThe resulting solid is filtered
  6. customdried in vacuo at 114° C. for 5 hours
  7. custom[α]D25 =-22.3° (c=1, DMF)

Sources & evidence

ORD record
ord-f79537f30f32433697e364a5ea5f6fcf
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

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