Sodium Carbonate → (3aR,10aS)-9-[4-(Benzyloxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361567Notes

Reaction equation

[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:13](=[O:14])[C@H:12]3[CH2:15][CH2:16][CH2:17][C@H:11]3[NH:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>ClCCl.O>[CH2:34]([O:33][C:31]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:13](=[O:14])[C@H:12]3[CH2:15][CH2:16][CH2:17][C@H:11]3[NH:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)=[CH:4][CH:3]=1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3aR*,10aS*)-9-(4-aminobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (3.64 g, 12 mmol) in dichloromethane (15 mL) was added a solution of sodium carbonate (1.88 g, 18 mmol) in water (15 mL) at 0° C. To this mixture was added benzyl chloroformate (2.0 mL, 14 mmol) at the same temperature and the mixture was stirred at 0° C. for 15 minutes. Upon phase separation, the aqueous layer was extracted with dichloromethane and the pooled organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to provide 4.18 g (yield 79%) of the title compound. m.p. 161.7°-162.5° C.

Workup

customUpon phase separation
extractionthe aqueous layer was extracted with dichloromethane
dry with materialthe pooled organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-b06216fd4e6741d293acfe1a0453a713
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866567

Reaction notes

Loading…