Diisopropylcarbodiimide → HCID 118204534, compound

HRID 529289Notes

Reaction equation

HRID 529289 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][CH3:22])[C:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C[C:26]2N(O)N=[N:29][C:27]=2[CH:28]=1.CC(C)N=C=NC(C)C.C1(N)CC1>CN(C=O)C>[CH:27]1([NH:29][C:11](=[O:13])[C:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:20][CH2:21][CH3:22])[CH2:28][CH2:26]1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 118204374HCID 118204374, compound

Product 1

HCID 118204534HCID 118204534, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-(tert-butoxycarbonylamino)-2,2-diethoxyhexanoic acid (8.03 g, 25.1 mmol) was dissolved under nitrogen in 400 mL DMF and HOBt (4.10 g, 30.3 mmol), DIC (7.7 mL, 49.7 mmol) and cyclopropylamine (3.5 mL, 50.0 mmol) were added to the reaction mixture. After stirring for 24 hours at room temperature, the mixture was quenched with 400 mL 5% NaCl and 800 mL EtOAc and the phases were separated. The aqueous phase was extracted with 100 mL EtOAc, the combined organic phases were dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography on silica gel (CHX:EE 10:1→3:1) yielded 3.2 g (S)-tert-butyl 1-(cyclopropylamino)-2,2-diethoxy-1-oxohexan-3-ylcarbamate.

Workup

  1. customthe mixture was quenched with 400 mL 5% NaCl and 800 mL EtOAc
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with 100 mL EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customPurification by column chromatography on silica gel (CHX:EE 10:1→3:1)

Sources & evidence

ORD record
ord-f69e85f266974389801aa4b18fa42497
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

Loading…