Triethylamine → HCID 13057009, compound

HRID 1759612Notes

Reaction equation

HRID 1759612 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]([C:21]([OH:23])=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:25][N:26](CC)CC.ClC(OCC(C)C)=O.Cl.CN>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]([C:21]([NH:26][CH3:25])=[O:23])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 151217tert-Butyloxycarbonyl-glycylphenylalanineHCID 6364545Methylamine hydrochloride

Product 1

HCID 13057009HCID 13057009, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of t-boc-gly-phe 7a (5.3 g, 1.6×10-2 mole) in dry THF (80 ml) under argon at -10° C. is added in turn Et3N (2.5 ml, 1.8×10-2 mole) and isobutyl chloroformate (2.4 ml, 1.8×10-2 mole). The resulting mixture is stirred at -10° C. for 10 minutes before a freshly neutrallized mixture of methylamine hydrochloride (3.3 g, 4.9×10-2 mole), Et3N (6.9 ml, 4.9×10-2 mole), THF (80 ml), and H2O (40 ml) is added in one portion. The cooling bath is then removed and the mixture allowed to warm to room temperature. After stirring overnight the reaction is quenched into saturated aqueous NaHCO3. The aqueous alkaline mixture is extracted with Et2O (3 times) and CH2Cl2 (2 times). The ethereal extracts are combined and subsequently washed with saturated aqueous NaCl as are the CH2Cl2 extracts. The ethereal and CH2Cl2 extracts are then combined and dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate gives a yellowish foam which when triturated with Et2O affords 8a as a colorless solid which crystallizes from aqueous ethanol as colorless matted needles, 4.1 g (74%), m.p. 158°-160° C. In a similar fashion, t-boc-gly-phe-leu-NHEt is prepared from 7a and leucine ethylamide.

Workup

  1. additionis added in one portion
  2. customThe cooling bath is then removed
  3. customis quenched into saturated aqueous NaHCO3
  4. extractionThe aqueous alkaline mixture is extracted with Et2O (3 times) and CH2Cl2 (2 times)
  5. washsubsequently washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration of the drying agent and evaporation of the filtrate
  8. customgives a yellowish foam which when
  9. customtriturated with Et2O

Sources & evidence

ORD record
ord-53a1921d8b1644b0aada6c6c843aa562
Source dataset
uspto-grants-1982_07
Patent number
US04341698

Reaction notes

Loading…