4-Methylmorpholine → 3-Tert-butoxycarbonyl-5(S)-{2-[N-(1-carbamoyl-1-methyl-ethyl)-carbamoyl]-2(S)-isopropyl-ethyl}-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

HRID 1779837Notes

Reaction equation

HRID 1779837 reaction equation
CN1CCOCC1.Cl.[NH2:9][C:10]([CH3:15])([CH3:14])[C:11]([NH2:13])=[O:12].[C:16]([O:20][C:21]([N:23]1[C@@H:27]([CH2:28][C@@H:29]([CH:45]([CH3:47])[CH3:46])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[C@H:26]([CH2:48][C@H:49]([C:53](O)=[O:54])[CH:50]([CH3:52])[CH3:51])[O:25][C:24]1([CH3:57])[CH3:56])=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[C:16]([O:20][C:21]([N:23]1[C@@H:27]([CH2:28][C@@H:29]([CH:45]([CH3:47])[CH3:46])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:32]=2)[C@H:26]([CH2:48][C@H:49]([C:53](=[O:54])[NH:9][C:10]([C:11](=[O:12])[NH2:13])([CH3:15])[CH3:14])[CH:50]([CH3:51])[CH3:52])[O:25][C:24]1([CH3:56])[CH3:57])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 145690092-Amino-2-methylpropanamide hydrochlorideHCID 236254795-Oxazolidinepropanoic acid, 3-[(1,1-dimethylethoxy)carbonyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-alpha-(1-methylethyl)-, (alphaS,4S,5S)-

Product 1

HCID 228657843-Tert-butoxycarbonyl-5(S)-{2-[N-(1-carbamoyl-1-methyl-ethyl)-carbamoyl]-2(S)-isopropyl-ethyl}-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

106 μl of 4-methyl-morpholine, 66 mg of 2-aminoisobutyric acid amide hydrochloride and 91 mg of O-benztriazol-1-yl-N,N,N','-tetramethyluronium hexafluorophosphate (HBTU) are added in succession to 119 mg of 3-tert-butoxycarbonyl-5(S)-(2(S)-carboxy-3-methyl-butyl)-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine (Example 124 c) in 8 ml of dimethylformamide. The reaction mixture is stirred for 8 days at 40° C. The mixture is concentrated by evaporation and the residue is partitioned between ethyl acetate and saturated sodium chloride solution. The organic phases are concentrated by evaporation and the residue is purified by means of FC (60 g of silica gel, dichloromethane/methanol=95:5). The title compound is obtained: Rf (dichloromethane/methanol=95:5)=0.30.

Workup

  1. concentrationThe mixture is concentrated by evaporation
  2. customthe residue is partitioned between ethyl acetate and saturated sodium chloride solution
  3. concentrationThe organic phases are concentrated by evaporation
  4. customthe residue is purified by means of FC (60 g of silica gel, dichloromethane/methanol=95:5)

Sources & evidence

ORD record
ord-c5e3732d33674a29988f51131b6511ed
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

Loading…