Water → HCID 70268268, compound

HRID 274810Notes

Reaction equation

HRID 274810 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([NH:14][CH:15]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:16]([NH:23][C:24]([NH:26][C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30]([O-:32])=[O:31])=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[OH-].[Li+].O>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([NH:14][CH:15]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:16]([NH:23][C:24]([NH:26][C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30]([OH:32])=[O:31])=[O:25])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 131718856HCID 131718856, compound

Product 1

HCID 70268268HCID 70268268, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl (-)-[S-(R*,R*)]-3-[[[[2-[[[[(4-methylphenyl)sulfonyl]amino]carbonyl]-amino]-1,2-diphenylethyl]amino]carbonyl]amino]benzoate (0.1 g, 0.17 mmol), in MeOH (5 mL) is added lithium hydroxide monohydrate (0.006 g, 0.17 mmol) followed by water to the cloud point. The resulting mixture is warmed to 50° C. for 4 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 185°-189° C. IR (KBr): 3383, 1699, 1558, 699 cm-1. NMR (DMSO-d6): δ2.31 (s, 3H), 4.87-5.04 (m, 2H), 6.84-7.72 (m, 19H), 8.07 (s, 1H), 8.77 (s, 1H), 10.65 (br s, 1H), 12.87 (br s, 1H). Analysis calculated for C30H28N4O6S.1.63H2O: C, 59.86; H, 5.23; N, 9.31. Found: C, 59.85; H, 4.96; N, 9.35. [α]D25 =-3.7° (c=1, DMF).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue partitioned between water and diethyl ether
  3. customThe layers are separated
  4. filtrationThe resulting solid is filtered
  5. customdried in vacuo at 114° C. for 5 hours
  6. custom[α]D25 =-3.7° (c=1, DMF)

Sources & evidence

ORD record
ord-d19b19b86ae84d30946a5624a9dd139c
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

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