Hydrochloric Acid → N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan

HRID 1198086Notes

Reaction equation

C[O:2][C:3](=[O:37])[CH:4]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[N:5]([CH2:19][O:20][CH:21]([Si:23]([CH3:26])([CH3:25])[CH3:24])[CH3:22])[C:6]([O:8][CH:9]1[CH:16]2[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:18][CH:10]1[CH2:11]3)[CH2:15]2)=[O:7].[Li+].[OH-].O1CCOCC1.Cl>O>[CH:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH:9]1[O:8][C:6]([N:5]([CH2:19][O:20][CH:21]([Si:23]([CH3:25])([CH3:24])[CH3:26])[CH3:22])[CH:4]([C:3]([OH:37])=[O:2])[CH2:27][C:28]1[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=1)=[O:7])[CH2:18]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-[(2-adamantyloxy)carbonyl]-α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester (4.5 g, 8.5 mmol), LiOH (0.22 g, 9.1 mmol), dioxane (90 mL), and water (30 mL) was stirred at 60° C. for 16 hours. After cooling, the reaction mixture was acidified to pH 4 with 1N hydrochloric acid and extracted with ethyl acetate. The organic extract was dried over Na2SO4 and then concentrated in vacuo. Trituration of the oily residue with diethyl ether gave the title compound as a white solid (4.0 g, 91.7%), mp 203° C. (dec.).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
extractionThe organic extract
dry with materialwas dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-be62031e91194f7bbb632bfc4d773345
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278316

Reaction notes

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