4-Methylmorpholine → HCID 59909776, compound

HRID 1350282Notes

Reaction equation

HRID 1350282 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:16][C:17]([CH3:24])=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=2)[CH2:11][C:12]([OH:14])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.[CH2:55]([O:62][NH2:63])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>>[CH2:55]([O:62][NH:63][C:12](=[O:14])[CH2:11][C@H:10]([C:15]1[O:16][C:17]([CH3:24])=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=1)[CH2:9][CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

6

Reactant 5

HCID 79724-Methylmorpholine2×HCID 102313O-BenzylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59909762HCID 59909762, compound

Product 1

HCID 59909776HCID 59909776, compoundYield 98.9%

Procedure

A solution of (3R)-6-cyclohexyl-3-[4-(methoxycarbonyl)-5-methyl-1,3-oxazol-2-yl]hexanoic acid (Preparation 174) (2.48 g, 7.36 mmol) was cooled to 0° and treated with 1-hydroxybenzotriazole hydrate (994 mg, 7.36 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.12 g, 11.06 mmol) and N-methylmorpholine (1.21 ml, 11.04 mmol). The mixture was stirred for 15 minutes then treated with O-benzylhydroxyamine (1.17 g, 7.36 mmol) and further N-methylmorpholine (0.81 ml, 7.36 mmol). The mixture was stirred for 1 hour being allowed to warm to room temperature over this time. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed sequentially with water, a saturated solution of sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as a colourless oil (3.22 g)

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed sequentially with water
  5. dry with materiala saturated solution of sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bcda859ada0f48739dc3c9b031e87589
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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