Hydrochloric Acid → tert-Butyl (S)-2-(7-chloro-1-oxoisoquinolin-2(1H)-yl)butanoate

HRID 1987863Notes

Reaction equation

HRID 1987863 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH:7]([N:10]1[CH:19](NC(C(OC(C)(C)C)=O)CC)[CH2:18][C:17]2[C:12](=[CH:13][C:14]([Cl:31])=[CH:15][CH:16]=2)[C:11]1=[O:32])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].Cl>C(O)(C)C.C(OCC)(=O)C.O>[Cl:31][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[CH:19][N:10]([C@@H:7]([CH2:8][CH3:9])[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:33])[C:11]2=[O:32])=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 665937472-[3-(1-tertButoxycarbonyl-propylamino)-7-chloro-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-butyric acid tert-butyl ester

Product 1

HCID 57725357tert-Butyl (S)-2-(7-chloro-1-oxoisoquinolin-2(1H)-yl)butanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-[3-(1-tertbutoxycarbonyl-propylamino)-7-chloro-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-butyric acid tert-butyl ester (8.58 g) in isopropanol (180 ml) at 0° C. was added concentrated hydrochloric acid (20 ml). The resulting mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was then diluted with ethyl acetate (500 ml) and water (150 ml). The organic phase was separated and washed with water, then brine, dried (magnesium sulfate), filtered and concentrated. The sub-title product was obtained as a yellow solid (5.57 g, 97%). m.p. 111.3-111.8° C.; [α]25D-52.30 (c=1, CHCl3); IR (solid) 1731.4, 1649.5, 1593.2, 1229.6, 1152.8, 901.9 cm−1; 1H NMR (400 MHz, CDCl3) δ 0.95 (3H, t), 1.48 (9H, s), 1.95 (1H, m), 2.30 (1H, m), 5.55 (1H, m), 6.40 (1H, m), 7.15 (1H, m), 7.49 (1H, m), 7.61 (1H, m), 8.40 (1H, m) ppm; 13C NMR (100 MHz, CDCl3) δ 10.9, 24.8, 28.1, 59.2, 82.8, 105.7, 127.3, 127.8, 128.1, 129.5, 133.1, 133.2, 135.4, 161.8, 170.2; MS ES(+) 322.4 (M+H).

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialbrine, dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81917c3174ae4312b3915d1959d274c5
Source dataset
uspto-grants-2009_06
Patent number
US07553852B2

Reaction notes

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