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

HRID 655821Notes

Reaction equation

HRID 655821 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 ambient 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, CDCl3); 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); 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. temperatureto warm to ambient and
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialbrine, dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10786b90fcb3485b816281c935ced91f
Source dataset
uspto-grants-2011_12
Patent number
US08071618B2

Reaction notes

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