Hydrochloric Acid → HCID 86749643, compound

HRID 1735459Notes

Reaction equation

HRID 1735459 reaction equation
C[O:2][C:3](=[O:57])[C@H:4]([CH2:53][CH2:54][S:55][CH3:56])[NH:5][C:6](=[O:52])[C@:7]([CH2:14][C@@H:15]([N:20]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:21][CH2:22][CH:23]([SH:43])[C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:16]([CH3:19])[CH2:17][CH3:18])([C@H:10]([CH2:12][CH3:13])[CH3:11])[NH:8][CH3:9].[OH-].[Na+].Cl>CO>[C:48]([O:47][C:45]([NH:44][N:20]([CH2:21][CH2:22][CH:23]([SH:43])[C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:15]([C@@H:16]([CH3:19])[CH2:17][CH3:18])[CH2:14][C@@:7]([C:6]([NH:5][C@H:4]([C:3]([OH:57])=[O:2])[CH2:53][CH2:54][S:55][CH3:56])=[O:52])([C@H:10]([CH2:12][CH3:13])[CH3:11])[NH:8][CH3:9])=[O:46])([CH3:51])([CH3:50])[CH3:49]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86749644HCID 86749644, compound

Product 1

HCID 86749643HCID 86749643, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2(S)-(2(R)-(t-butoxycarbonylamino-3-triphenylmethyl mercaptopropylamino)-3(S)-methylpentyl]-N-methyl-isoleucyl-methionine methyl ester (0.19 g, 0.232 mmol, prepared as an intermediate in Example 5) was dissolved in MeOH (4 mL), treated with 1N NaOH soln (0.927 mL, 0.927 mmol), and stirred for 3.5 h at ambient temperature. The reaction mixture was concentrated, the residue dissolved in H2O (20 mL), neutralized with 1N HCl (0.927 mL, 0.927 mmol), and extracted with EtOAc (3×20 mL). The organic layers were combined, washed with brine, and dried (Na2SO4). Filtration and concentration to dryness gave 0.18g (96%) of the title compound which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in H2O (20 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-beacb50cb9eb42e79b8d4b82230ced07
Source dataset
uspto-grants-1996_07
Patent number
US05536750

Reaction notes

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