Hydrochloric Acid → HCID 19003122, compound

HRID 2259285Notes

Reaction equation

HRID 2259285 reaction equation
CC(C)(OC([NH:7][CH:8]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)=[O:10])=O)C.[ClH:32]>O1CCCC1>[ClH:32].[NH2:7][CH:8]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:9]([O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19003132HCID 19003132, compound

Product 1

HCID 19003122HCID 19003122, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethylbenzyl 2-(1,1-dimethylethoxycarbonylamino)-3-(3-indolyl)propionate (1.0 g) was dissolved in dry tetrahydrofuran (20 ml). Saturated methanolic hydrochloric acid (10 ml) was added and the reaction was stirred for 16 hours. The solvent was removed in vacuo and the residue was recrystallised from ethanol/diethyl ether to yield 3,5-dimethylbenzyl 2-amino-3-(3-indolyl)propionate hydrochloride (0.71 g), m.p. 213°-214° C. 1H NMR (360 MHz D6DMSO) δ11.09 (1H, s), 8.64 (1H, s), 7.51 (1H, d, J=7 Hz), 7.38 (1H, d, J=7 Hz), 7.20 (1H, d, J=2 Hz), 7.10 (1H, t, J=7 Hz), 6.98 (1H, t, J=7 Hz), 6.94 (1H, s), 6.76 (2H, s). Found: C, 66.25; H, 6.67; N, 7.71, C20H22N2O2. HCl. 0.25(H2O) requires C, 66.11; H, 6.52; N, 7.71%.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was recrystallised from ethanol/diethyl ether

Sources & evidence

ORD record
ord-ac2b9d79df704e65a262fb470f21ec84
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

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