Hydrochloric Acid → HCID 178445975, compound

HRID 255614Notes

Reaction equation

HRID 255614 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:37]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@@H:38]([OH:45])[CH2:39][C:40]([O:42]CC)=[O:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:37]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@@H:38]([OH:45])[CH2:39][C:40]([OH:42])=[O:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178471826HCID 178471826, compound

Product 1

HCID 178445975HCID 178445975, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

112 mg (0.17 mmole) of ethyl 4(S)-[N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidyl]amino-3(S)-hydroxy-6-methylheptanoate (prepared as described in Example 1) were dissolved in 3 ml of methanol, and 0.2 ml (0.2 mmole) of a 1N aqueous solution of sodium hydroxide was added to the resulting solution. The mixture was then stirred at room temperature for 6 hours, after which it was neutralized by the addition of 1N aqueous hydrochloric acid. The solvent was then removed from the resulting solution by distillation under reduced pressure. To the solid residue were added 5 ml of water and 2 ml of ethyl acetate to form a precipitate, which was crushed and separated by filtration. The resulting residue was washed with water and with a small amount of ethyl acetate, and then dried to give 49 mg of the title compound as a white powder, melting at 191°-192° C., [α]24 -59.2° (C=0.3, methanol).

Workup

  1. customThe solvent was then removed from the resulting solution by distillation under reduced pressure
  2. additionTo the solid residue were added 5 ml of water and 2 ml of ethyl acetate
  3. customto form a precipitate, which
  4. customwas crushed
  5. customseparated by filtration
  6. washThe resulting residue was washed with water and with a small amount of ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-dbc70cab3111468387ba85d30845c26b
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

Loading…