Isopropylamine → HCID 13454826, compound

HRID 986615Notes

Reaction equation

HRID 986615 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1[CH:22]=[C:21]2[N:23]=NN(O)[C:20]2=CC=1.O.C1CCC(N=C=NC2CCCCC2)CC1.C(N)(C)C>CN(C=O)C.CC(O)=O>[CH:21]([NH:23][C:14](=[O:16])[C@@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:22])[CH3:20]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 10868DicyclohexylcarbodiimideHCID 70832N-Cbz-d-alanineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 13454826HCID 13454826, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

N-Benzyloxycarbonyl-D-alanine (2.232 g, 10 mmol) and HOBt hydrate (1.53 g, 10 mmol) are dissolved in 40 mL freshly distilled DMF and cooled in an ice-H2O bath. DCC (2.06 g, 10 mmol) is added. The reaction mixture is stirred in the cold for 15 minutes, isopropylamine (0.85 mL, 10 mmol) is then introduced. It is stirred in the cold for 2 hours and room temperature overnight. HOAc (a few drops) is added and the reaction mixture stirred at room temperature for another 15 minutes. It is filtered to remove DCU and the filtrate layered with 50 mL EtOAc and 80 mL H2O. The phases are separated and the aqueous phase is extracted with 50 mL EtOAc. The pooled EtOAc extract is wazhed with H2O, 0.1N HCl (3×), H2O (3×), 0.1N NaOH (3×), H2O (3×), dried over anhydrous Na2SO4 and evaporated to dryness. The crude product is purified by liquid column chromatography on silica gel eluting with toluene/EtOAc mixtures.

Workup

  1. temperaturecooled in an ice-H2O bath
  2. stirringIt is stirred in the cold for 2 hours
  3. customroom temperature overnight
  4. stirringthe reaction mixture stirred at room temperature for another 15 minutes
  5. filtrationIt is filtered
  6. customto remove DCU
  7. customThe phases are separated
  8. extractionthe aqueous phase is extracted with 50 mL EtOAc
  9. extractionThe pooled EtOAc extract
  10. dry with materialdried over anhydrous Na2SO4
  11. customevaporated to dryness
  12. customThe crude product is purified by liquid column chromatography on silica gel eluting with toluene/EtOAc mixtures

Sources & evidence

ORD record
ord-7844646145eb45d98046de297af58a25
Source dataset
uspto-grants-1987_12
Patent number
US04714619

Reaction notes

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