4-Methylmorpholine → HCID 57079181, compound

HRID 1700990Notes

Reaction equation

HRID 1700990 reaction equation
CN(CCCN=C=NCC)C.[C:12]([O:16][C:17](=[O:26])[CH2:18][C@@H:19]([CH2:23][CH:24]=[CH2:25])[C:20]([OH:22])=O)([CH3:15])([CH3:14])[CH3:13].[CH2:27]([O:34][C:35](=[O:42])[C@H:36]([C:38]([CH3:41])([CH3:40])[CH3:39])[NH2:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1>ClCCl.C(OCC)(=O)C>[CH3:39][C:38]([CH3:41])([CH3:40])[C@H:36]([NH:37][C:20]([C@H:19]([CH2:23][CH:24]=[CH2:25])[CH2:18][C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:26])=[O:22])[C:35]([O:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:42]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10560578(R)-2-(2-(tert-butoxy)-2-oxoethyl)pent-4-enoic acidHCID 10858138(S)-Benzyl 2-amino-3,3-dimethylbutanoate

Product 1

HCID 57079181HCID 57079181, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(Dimethylaminopropyl)-N′-ethylcarbodiimide (2.298 g, 12 mmol) was added to a stirred mixture of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]pent-4-enoic acid (2.13 g, 10 mmol tert-leucine benzyl ester (2.834 g, 11 mmol)(N. Moss et al., J. Med. Chem., 1996, 39, 2178), N-methylmorpholine (2.40 mL, 22 mmol) and 1-hydroxybenzotriazole hydrate (1.836 g, 12 mmol) in anhydrous dichloromethane (50 mL) under nitrogen at 0° C. The mixture was allowed to warm slowly to room temperature with the cooling bath in place. After 20 h, the mixture poured into ethyl acetate (250 mL) and washed with 5% aqueous citric acid (2×100 mL), saturated aqueous sodium bicarbonate (2×70 mL), brine (70 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil crystallised upon addition of pentane. The solid was filtered and dried to give tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)hex-5-enoate (4.068 g, 97%), as a colourless solid.

Workup

  1. washwashed with 5% aqueous citric acid (2×100 mL), saturated aqueous sodium bicarbonate (2×70 mL), brine (70 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residual oil crystallised upon addition of pentane
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-554498012b0c4edead7f3de15aac027b
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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