Hydrochloric Acid → HCID 86755496, compound

HRID 2287520Notes

Reaction equation

HRID 2287520 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:28][CH3:29])=[C:8]([CH:27]=1)[CH2:9][NH:10][C@H:11]1[C@H:15]([C:16]([O:18]C)=[O:17])[C@@H:14]([CH3:20])[NH:13][C@H:12]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:3])[CH3:2].[ClH:30]>>[ClH:30].[ClH:30].[C:16]([C@@H:15]1[C@@H:14]([CH3:20])[NH:13][C@@H:12]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:11]1[NH:10][CH2:9][C:8]1[CH:27]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=[CH:6][C:7]=1[O:28][CH3:29])([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 15454893HCID 15454893, compound

Product 1

HCID 86755496HCID 86755496, compoundYield 96%

Procedure

A solution of (2S*,3S*,4R*,5R*)-3-[N-(5-isopropyl-2-methoxybenzyl)amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (0.39 g, 0.98 mmol) in 6M HCl aq. solution (6.0 ml) was stirred and heated at a gentle reflux for 30 minutes, wherein precipitation of white solids initiated ca. 10 minutes after refluxing. The reaction mixture was cooled to room temperature, and then EtOH (4.0 ml) was added. After the mixture was ice-cooled for 30 minutes, the white precipitates were filtered off, washed with EtOH (×2), and dried in vacuo at a temperature between 40 and 50 C. for 2 days to afford title compound (0.43 g, 96%) as white needles. ##STR7## mp 159-164 C.: IRmax (nujol): 3400(s), 3200(s), 3130(s), 2370(s), 2300(br., s), 1735(s), 1710(s), 1585(s), 1510(s), 1260(s), 1143(s), 1017(s), 830(s), 770(s), 745(s), 702(s) cm-1 ; 1H-NMR δ (DMSO-d6): 7.907.73(m, 2H), 7.60-7.45(m, 3H), 7.25-7.13(m, 2H), 6.90(d, J=9.2 Hz, 1H), 5.35-5.15(m, 1H), 4.63-4,41(m, 1H), 4.20-4.01(m, 1H), 4.00-3.83(m, 1H), 3.803.15(m, 1H), 3.67(s, 3H), 2.79(sep, J=6.8 Hz, 1H), 2.55-2.42(m, 1H), 1.71(br.d, J=5.9 Hz, 3H), 1.15(d, J=6.8 Hz, 6H) ppm.

Workup

  1. temperatureheated at
  2. temperaturea gentle reflux for 30 minutes
  3. customwherein precipitation of white solids
  4. temperatureafter refluxing
  5. additionEtOH (4.0 ml) was added
  6. temperaturecooled for 30 minutes
  7. customthe white precipitates
  8. filtrationwere filtered off
  9. washwashed with EtOH (×2)
  10. customdried in vacuo at a temperature between 40 and 50 C

Sources & evidence

ORD record
ord-3046b5c8269f491197178bb4e55ec15b
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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