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

HRID 1091428Notes

Reaction equation

HRID 1091428 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 −52.3° (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-d8bb44e0b2614a9e9d764682633ea1d2
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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