Water → HCID 13338741, compound

HRID 2417838Notes

Reaction equation

[C:1]1(=[O:24])[N:5]([CH:6]2[CH2:13][CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]2=[O:18])[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.CC(C)([O-])C.[K+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].O>CN(C)C=O>[CH2:36]([O:35][C:33]([CH2:32][N:8]1[C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[CH2:11][CH2:12][CH2:13][CH:6]([N:5]2[C:4](=[O:19])[C:3]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]3[C:1]2=[O:24])[C:7]1=[O:18])=[O:34])[CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-phthalimido-3,4,5,6-tetrahydro-1-benzazocin-2(1H)one (1.7 g) in dimethylformamide (10 ml) is stirred at 0° C. under a nitrogen atmosphere. A solution of potassium t-butoxide (0.75 g) in dimethylformamide (6 ml) is added and the reaction mixture is stirred at 0° C. for five minutes. A solution of ethyl bromoacetate (1.0 g) in dimethylformamide (5 ml) is added and the reaction mixture stirred at 0° C. for 11/2 hours. Water (3 ml) is added, and the reaction mixture is evaporated under high vacuum. The residue is distributed between ethyl acetate (100 ml) and water (50 ml) and the aqueous layer is washed with water (50 ml) and dried over sodium sulfate. The residue is recrystallized from methanol/ether to give 1-ethoxycarbonylmethyl-3-phthalimido-3,4,5,6-tetrahydro-1-benzazocin-2(1H)one, mp 79°-81° C. used in the next synthetic step.

Workup

stirringthe reaction mixture stirred at 0° C. for 11/2 hours
customthe reaction mixture is evaporated under high vacuum
washthe aqueous layer is washed with water (50 ml)
dry with materialdried over sodium sulfate
customThe residue is recrystallized from methanol/ether

Sources & evidence

ORD record: ord-d0b9bc56dd3f440ba7e901a1ec57446d
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04470988

Reaction notes

Loading…