Triethylamine → HCID 86620557, compound

HRID 2054006Notes

Reaction equation

HRID 2054006 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:10][CH2:11][C:12]([O-:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.C(N(CC)CC)C.[N+:40](=[CH2:42])=[N-:41]>O1CCCC1.C(O)(=O)C.C(OC)(C)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH2:11][C:12](=[O:14])[CH:42]=[N+:40]=[N-:41])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9550DiazomethaneHCID 62365Isobutyl chloroformateHCID 7017888HCID 7017888, compound

Product 1

HCID 86620557HCID 86620557, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

5.0 g (14.9 mmol) of 1-benzyl tert-butoxycarbonyl-(S)-glutamate is placed in 75 mL of tetrahydrofuran while cooling with ice, combined with 2.1 mL (16.5 mmol) of isobutylchloroformate and 2.5 mL (18 mmol) of triethylamine, and stirred for 60 minutes. Then 30 mL, (20 mmol) of diazomethane (0.7 molar in diethyl ether) and 200 mL of tert-butylmethylether are added and the mixture is stirred overnight at ambient temperature. After the addition of 1 mL glacial acetic acid, the phases are separated, and the organic phase is dried and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with dichloromethane/ethyl acetate (0%-20%). Yield: 2.2 g (41%); Rf value: 0.42 (silica gel: petroleum ether/ethyl acetate=6:4); C18H23N3O5 (361.40); mass spectrum: (M+H)+=362

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture is stirred overnight at ambient temperature
  3. customthe phases are separated
  4. customthe organic phase is dried
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel
  7. washeluting with dichloromethane/ethyl acetate (0%-20%)

Sources & evidence

ORD record
ord-1b9be11135ed43a39533553185fc431e
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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