Sodium Hydroxide → HCID 10347845, compound

HRID 1707325Notes

Reaction equation

HRID 1707325 reaction equation
C[O:2][C:3](=[O:41])[C@H:4]([C@H:37]([CH2:39][CH3:40])[CH3:38])[NH:5][CH2:6][C@@H:7]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>CO>[C:33]([O:32][C:30]([NH:29][C@@H:7]([CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:6][NH:5][C@H:4]([C:3]([OH:41])=[O:2])[C@H:37]([CH2:39][CH3:40])[CH3:38])=[O:31])([CH3:35])([CH3:36])[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 18655303HCID 18655303, compound

Product 1

HCID 10347845HCID 10347845, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2(R)-(t-butoxycarbonyl)amino-3-triphenylmethylmercaptopropyl]-L-isoleucine methyl ester (1.63 g, 0.0028 mol) was dissolved in MeOH (50 mL) and 1N NaOH solution (11.23 mL, 0.0112 mol) was added with stirring at ambient temperature. After 4 h,.solid NaOH (2.0 g) was added and stirring was continued for 16 h. The reaction mixture was concentrated to remove MeOH and extracted with EtOAc (2×100 mL). The extract was washed with brine and dried (Na2SO4). Filtration and concentration to dryness gave 1.6 g of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. concentrationThe reaction mixture was concentrated
  4. customto remove MeOH
  5. extractionextracted with EtOAc (2×100 mL)
  6. washThe extract was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-236ecb4d9ef44eb9bc38eba4de333fc1
Source dataset
uspto-grants-1994_10
Patent number
US05352705

Reaction notes

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