Hydrochloric Acid → HCID 70010726, compound

HRID 1368763Notes

Reaction equation

HRID 1368763 reaction equation
[OH:1][C@@H:2]([C@@H:21]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])C)=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[NH:4][CH2:5][CH:6]([CH3:8])[CH3:7].Cl.C(N([CH2:43][CH3:44])CC)C.[Cl-].[Na+].[OH2:47]>C(Cl)Cl>[OH:1][C@@H:2]([C@@H:21]([NH:29][C:30]([O:32][C@H:33]1[CH2:36][CH2:44][CH2:43][O:47][CH2:35]1)=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)(=[O:10])=[O:11])[NH:4][CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 57417360Sodium chloride; waterHCID 70010713HCID 70010713, compound

Product 1

HCID 70010726HCID 70010726, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2(S)-hydroxy-3(S)-(t-butyloxycarbonyl)amino-1-(4-nitrobenzenesulfonyl)-1-isobutylamino-4-phenylbutane (93 mg, 0.19 mmol) in 1 mL of dry CH2Cl2 was passed anhydrous HCl gas for 0.5 h. After removal of HCl gas bubbler, the mixture was stirred for 1 h. The solvent was removed in vaccuo and the residue was dissolved in 1 mL of dry CH2Cl2. To the mixture were added triethylamine (30 μl, 0.23 mmol) and N-succinimidyl (S)-(+)-3-hydroxytetrahydrofuran carbonate (44 mg, 0.19 mmol) at room temperature. The mixture was stirred for 4 h until no starting material remained by TLC and it was poured into brine (2 mL) and extracted with EtOAc (10 mL). The organic extract was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude compound was recrystallized in ethyl acetate to give 86 mg of 2(S)-hydroxy-3(S)-[3(S)-tetrahydropyranyloxycarbonyl]amino-1-(4-nitrobenzenesulfonyl)-1-isobutylamino-4-phenylbutane.

Workup

  1. customfor 0.5 h
  2. customAfter removal of HCl gas bubbler
  3. customThe solvent was removed in vaccuo
  4. dissolutionthe residue was dissolved in 1 mL of dry CH2Cl2
  5. stirringThe mixture was stirred for 4 h until no starting material
  6. extractionextracted with EtOAc (10 mL)
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude compound was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-cc18f1cb5208498caec5479a90157fa2
Source dataset
uspto-grants-2003_06
Patent number
US06573388B1

Reaction notes

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