Hydrochloric Acid → HCID 18660170, compound

HRID 1741497Notes

Reaction equation

HRID 1741497 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][N:5]([CH:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:15]1[CH2:19][CH2:18][CH2:17][NH:16]1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].[OH-].[Na+].Cl>CO>[C:23]([O:22][C:20]([CH:14]([C@@H:15]1[CH2:19][CH2:18][CH2:17][NH:16]1)[N:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH2:4][C:3]([OH:27])=[O:2])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18660171HCID 18660171, compound

Product 1

HCID 18660170HCID 18660170, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[(t-Butyloxycarbonyl)-pyrrolidin-2(S)-ylmethyl]-(N-2-methylbenzyl)-glycine methyl ester (41.85 g, 0.111 mol) was dissolved in CH3OH (300 mL) at 0° C. and treated with 2 N NaOH solution (111 mL, 0.222 mol) and allowed to stir at ambient temperature for 3 hr. 1 N HCl (235 mL, 0.235 mol) was added, the CH3OH was removed on a rotary evaporator, and the residue was extracted with EtOAc (2×1.5 L), washed with brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound as a white solid. 1H NMR (CD3OD ) δ 7.56 (d, 1H, J=7.5 Hz), 7.15-7.36 (m, 3H), 4.70 (d, 1H, J=13 Hz), 4.27 (d, 1H, J=13 Hz), 4.1-4.2 (m, 1H), 3.73 (d, 1H, J=16 Hz), 3.59 (d, 1H, J=16 Hz), 3.15-3.5 (m, 4H), 2.49 (s, 3H), 2.1-2.2 (m, 1H), 1.7-1.9 (m, 2H), 1.6-1.7 (m, 1H), 1.46 (s, 9 h).

Workup

  1. customthe CH3OH was removed on a rotary evaporator
  2. extractionthe residue was extracted with EtOAc (2×1.5 L)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-0876229cdfcd45a181e43c970c0767e4
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

Loading…