Hydrochloric Acid → HCID 86756536, compound

HRID 1532035Notes

Reaction equation

HRID 1532035 reaction equation
C(OC([NH:8][CH:9]([CH2:20][C:21]1[C:22]([O:36][CH2:37][CH3:38])=[N:23][O:24][C:25]=1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=O)(C)(C)C.[ClH:39]>C(OCC)C>[ClH:39].[NH2:8][CH:9]([CH2:20][C:21]1[C:22]([O:36][CH2:37][CH3:38])=[N:23][O:24][C:25]=1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54182839HCID 54182839, compound

Product 1

HCID 86756536HCID 86756536, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of benzyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-(5-benzyloxycarbonyl-3-ethoxyisoxazol-4-yl)propionate (1.9 g, 3.6 mmol) and a saturated solution of HCl in dietyl ether (40 mL) was boiled under reflux for 2 h. The formed crystals were collected by filtration, stirred with ethyl acetate, and collected by filtration (0.53 g, 32%): mp 142-144° C.; 1H NMR (DMSO-d6) δ1.32 (t, 3 H), 3.17 (dd, 1 H), 3.25 (dd, 1 H), 4.17-4.32 (m, 3 H), 5.09 (dd, 2 H), 5.39 (s, 2 H), 7.24-7.53 (m, 10 H); MS ((M+H)+) m/z 425. Anal. calcd, C, 59.93; H, 5.48; N, 6.08; found, C, 59.70; H, 5.49; N, 6.26.

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationThe formed crystals were collected by filtration
  3. filtrationcollected by filtration (0.53 g, 32%)

Sources & evidence

ORD record
ord-7c9bc1f9b11f4153a229ab03fa1af850
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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