Hydrochloric Acid → HCID 22858731, compound

HRID 2396086Notes

Reaction equation

HRID 2396086 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C@@H:10]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:11][S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].Cl>CO>[C:36]([O:35][C:33]([NH:32][C@@H:10]([CH2:11][S:12][C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:3]([OH:40])=[O:2])=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22858732HCID 22858732, compound

Product 1

HCID 22858731HCID 22858731, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[2(R)-(t-butyloxycarbonyl)amino-3-triphenylmethylmercaptopropyl]-L-proline methyl ester (0.325 g, 0.58 mmol) was dissolved in MeOH (12 mL) and 1N NaOH solution (2.3 mL, 2.3 mmol) with stirring at ambient temperature. After 24 hrs, the reaction mixture was concentrated to remove MeOH, then dissolved in H2O, neutralized with 1N HCl (2.3 mL, 2.3 mmol), and extracted with EtOAc (3×10 mL). The organics were combined, washed with brine and dried (Na2SO4). Filtration and concentration to dryness provided the title compound. 1H NMR (CD3OD) δ 7.2-7.5 (m, 15H), 3.7-3.85 (m, 1H), 3.5-3.7 (m, 2H), 2.9-3.15 (m, 3H), 2.2-2.6 (m, 3H), 1.8-2.2 (m, 3H), 1.48 (s, 9H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto remove MeOH
  3. dissolutiondissolved in H2O
  4. extractionextracted with EtOAc (3×10 mL)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-53173854d4694983a1ae899590b3e244
Source dataset
uspto-grants-1996_02
Patent number
US05491164

Reaction notes

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