Triethylamine → N-[N-(benzyloxycarbonyl)-N-methylvalyl]-L-aspartic acid di-tert-butyl ester

HRID 529212Notes

Reaction equation

HRID 529212 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:19])[C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:21]([O:25][C:26](=[O:37])[C@H:27]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH2:28])([CH3:24])([CH3:23])[CH3:22].CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1>[C:21]([O:25][C:26](=[O:37])[C@H:27]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:28][C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[N:11]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:19])([CH3:23])([CH3:24])[CH3:22]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 13768146L-Aspartic acid, bis(1,1-dimethylethyl) ester, hydrochloride

Product 1

HCID 86714692N-[N-(benzyloxycarbonyl)-N-methylvalyl]-L-aspartic acid di-tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-benzyloxycarbonyl-N-methyl-L-valine (0.50 g, 1.9 mmol), L-aspartic acid di-tert-butyl ester hydrochloride (0.53 g, 1.9 mmol), WSC hydrochloride (0.43 g, 2.3 mmol), and 1-hydroxybenzotriazole monohydrate (0.35 g, 2.3 mmol) were added tetrahydrofuran (10 ml) and triethylamine (0.39 mL, 2.8 mmol), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20) to give the title compound (0.91 g, 1.8 mmol, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-1bef1f4f027c4f7fac8c0efe7fef9521
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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