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Triethylamine → HCID 11439448, compound

HRID 1828957
Notes
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Reaction equation

HRID 1828957 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([O:12][CH3:13])=[O:11].C(N(CC)CC)C.[C:21]([O:25][C:26]([NH:28][C@H:29]([C:31](O)=[O:32])[CH3:30])=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:21]([O:25][C:26]([NH:28][C@@H:29]([CH3:30])[C:31]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([O:12][CH3:13])=[O:11])=[O:32])=[O:27])([CH3:24])([CH3:23])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 7020378methyl (2S)-2,3-dihydro-1H-indole-2-carboxylate

Product 1

HCID 11439448HCID 11439448, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

There are introduced into a reactor, with stirring, 2.13 kg of methyl(2S)-2,3-dihydroindole-2-carboxylate, 1 kg of triethylamine, 30 litres of tetrahydrofuran and then, after 10 minutes' stirring at room temperature, 1.9 kg of N-[tert-butyloxycarbonyl]-(S)-alanine and 2 kg of dicyclohexylcarbodiimide. The heterogeneous mixture is then stirred at room temperature for 6 hours, and is subsequently cooled to 0° C. and filtered.

Workup

  1. additionThere are introduced into a reactor
  2. stirringThe heterogeneous mixture is then stirred at room temperature for 6 hours
  3. filtrationfiltered

Sources & evidence

ORD record
ord-49236bcd7962412f9cc400bac6d0e01a
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07060842B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes