Ammonia → benzyl N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate

HRID 1746587Notes

Reaction equation

HRID 1746587 reaction equation
O=C1CCC(=O)N1O[C:9](=[O:32])[C@H:10]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[NH3:33]>C1COCC1>[CH2:15]([O:14][C:12]([NH:11][C@H:10]([C:9]([NH2:33])=[O:32])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11048356Z-Trp-OSu

Product 1

HCID 853880benzyl N-[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To THF (150 mL) solution of Nα-benzyloxycarbonyl-L-tryptophan-2,5-dioxopyrrolidin-1-yl ester (5.0 g) was added dropwise a 30% aqueous ammonia (3.3 mL) at 0° C., and thereafter the mixture was stirred for 2 hours at room temperature. The crystals were distilled off, and thereafter to the residue obtained by distilling off the solvent of the filtrate under a reduced pressure was added petroleum ether and a small amount of diethyl ether, and the crystals precipitated were filtered, to give the captioned compound (3.6 g, 91%).

Workup

  1. distillationThe crystals were distilled off
  2. customto the residue obtained
  3. distillationby distilling off the solvent of the filtrate under a reduced pressure
  4. additionwas added petroleum ether
  5. customa small amount of diethyl ether, and the crystals precipitated
  6. filtrationwere filtered

Sources & evidence

ORD record
ord-ca46140eb77f4312a677f5c17db6de9e
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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