Hydrochloric Acid → HCID 54517139, compound

HRID 1440396Notes

Reaction equation

HRID 1440396 reaction equation
C[O:2][C:3](=[O:37])[C@H:4]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[NH:5][C:6](=[O:26])[C@H:7]([C@H:22]([CH2:24][CH3:25])[CH3:23])[NH:8][S:9]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].C1COCC1.[OH-].[K+].Cl>O.CO>[C:12]1([S:9]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:37])=[O:2])[CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=2)=[O:26])[C@H:22]([CH2:24][CH3:25])[CH3:23])(=[O:11])=[O:10])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 54110952HCID 54110952, compound

Product 1

HCID 54517139HCID 54517139, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cooled mixture of N-(1-naphthylsulfonyl)-(L)-isoleucyl-(L)-tryptophan methyl ester (6.9 g) and THF (40 ml)-methanol (20 ml) was added dropwise a solution of KOH (1.5 g) in water (10 ml). After stirring at 0° C. for 20 hours, the reaction mixture was acidified with 1N HCl (35 ml) with ice-cooling, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried (MgSO4). The organic solvent was evaporated off to yield N-(1-naphthylsulfonyl)-(L)-isoleucyl-(L)-tryptophan (6.6 g, 98%) as crystals. Melting point: 167°-168° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe organic solvent was evaporated off

Sources & evidence

ORD record
ord-199350b4feb04be6a928c3cc97a998b0
Source dataset
uspto-grants-1996_03
Patent number
US05498728

Reaction notes

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