4-Methylmorpholine → HCID 59909850, compound

HRID 1279882Notes

Reaction equation

HRID 1279882 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:31])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:30])=[C:25]([C:27](O)=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:63][O:64][C:65](=[O:68])[CH2:66][NH2:67]>ClCCl>[CH2:1]([O:8][NH:9][C:10](=[O:31])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:30])=[C:25]([C:27]([NH:67][CH2:66][C:65]([O:64][CH3:63])=[O:68])=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-Methylmorpholine2×HCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59909759HCID 59909759, compound

Product 1

HCID 59909850HCID 59909850, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)5-methyl-1,3-oxazole-4-carboxylic acid (Preparation 72) (230 mg, 0.53 mmol), N-methylmorpholine (61 l, 0.56 mmol), 1-hydroxybenzotriazole hydrate (68 mg, 0.53 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (107 mg, 0.56 mmol) in dichloromethane (10 ml) was treated with a solution of glycine methyl ester hydrochloride (70 mg, 0.56 mmol) and N-methylmorpholine (61 l, 0.56 mmol) in dichloromethane (2 ml) and stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:ammonia) gradually changing to 98:2:0.2 (dichloromethane:methanol:ammonia) to afford the title compound as a white solid (160 mg).

Workup

  1. washwashed with water, saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:ammonia)

Sources & evidence

ORD record
ord-a02c1bcd33f340d9abf0c2f76cea5433
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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