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

HRID 1198086
Notes
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Reaction equation

HRID 1198086 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 86747503N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

Product 1

HCID 86747505N-[(2-Adamantyloxy)carbonyl]-alpha-trimethylsilylethoxymethyl-DL-tryptophanYield 91.8%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

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

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes