Hydrochloric Acid → HCID 67628384, compound

HRID 1598477Notes

Reaction equation

HRID 1598477 reaction equation
[CH2:1]([NH:8][C:9](=[O:23])[C@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:25](OCC)(=O)[CH3:26]>C1COCC1>[CH2:1]([N:8]1[CH:26]=[CH:25][N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:10]([CH2:11][CH2:12][CH2:13][CH3:14])[C:9]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 22884173HCID 22884173, compound

Product 1

HCID 67628384HCID 67628384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-benzyl 2(R)-tert-butoxycarbonylaminohexanamide (1.0 g, 2.29 mmol) in THF (10 mL) was vigorously stirred with 6N HCl(10 mL) for 24h. Ethyl acetate was added, and the layers separated. The organic phase was washed with water, then saturated sodium chloride solution. The crude product was chromatographed on silica gel with 30% ethyl acetate in hexane. The title compound was obtained as an oil (0.140 g). NMR (CDCl3, 300 MHz) δ 7.3 (5H, m), 6.31, 6.14 (1H, 2 ds, J=7, 7 Hz), 5.55, 5.42 (1H, 2 ds, J=7, 7 Hz), 4.68 (2H, AB q, J=15 Hz, D n=36 Hz), 4.78 (1H, m), 1.66 (2H, m), 1.47 (9H, d), 1.33 (4H, m), 0.89 (3H, brt, J=7 Hz).

Workup

  1. customthe layers separated
  2. washThe organic phase was washed with water
  3. customThe crude product was chromatographed on silica gel with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9fd248781e2a490b96e7f1555a2aa3e2
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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