Hydrochloric Acid → 2-(S)-amino-N-[3-(1H-indol-3-yl)-propyl]-butyramide

HRID 1039028Notes

Reaction equation

HRID 1039028 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:33])[C@@H:22]([NH:25]C(OC(C)(C)C)=O)[CH2:23][CH3:24])=[CH:9]1)=O)(C)(C)C.ClCCl.Cl>C(OCC)C>[NH2:25][C@@H:22]([CH2:23][CH3:24])[C:21]([NH:20][CH2:19][CH2:18][CH2:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][CH:9]=1)=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 672353373-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 532523192-(S)-amino-N-[3-(1H-indol-3-yl)-propyl]-butyramide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 20 mL cintillation vial was charged with 3-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester (280 mg, 0.61 mmol), dichloromethane (3.6 mL), and 1M hydrogen chloride in diethyl ether (3.0 mL). The resulting mixture was stirred at room temperature for 4 h, then concentrated in-vacuo and the residue placed under high vacuum overnight to yield 2-(S)-amino-N-[3-(1H-indol-3-yl)-propyl]-butyramide. 1H NMR (300 MHz, CD3OD) δ 7.51 (d, J=7.8 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 6.95-7.09 (m, 3H), 3.11-3.39 (m, 3H), 2.77-2.82 (m, 2H), 1.78-2.01 (m, 4H), and 0.94 (t, J=7.4 Hz, 3H); MS (ES+) 260 (M+1).

Workup

  1. concentrationconcentrated in-vacuo
  2. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-434a662930954dbc89960f308da74fbb
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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