4-Methylmorpholine → HCID 86746721, compound

HRID 1590353Notes

Reaction equation

HRID 1590353 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([NH:22][C@H:23]([C:31]([C@:33]([C@H:38]([C@@H:40]([C@@H:42]([CH2:44][NH2:45])[OH:43])[OH:41])[OH:39])([OH:37])[C:34]([OH:36])=[O:35])=[O:32])[CH2:24][S:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29])=[O:21])[CH2:10][CH:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:12](=[O:14])[OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH3:61][Si:62]([CH:65](O)[CH3:66])([CH3:64])[CH3:63]>CN(C)C=O>[CH3:61][Si:62]([CH2:65][CH2:66][O:35][C:34]([C@@:33]([C:31](=[O:32])[C@H:23]([CH2:24][S:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29])[NH:22][C:20](=[O:21])[C@H:9]([CH2:10][CH:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:12](=[O:13])[OH:14])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])([C@H:38]([C@@H:40]([C@@H:42]([CH2:44][NH2:45])[OH:43])[OH:41])[OH:39])[OH:37])=[O:36])([CH3:64])[CH3:63]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 124478981-(Trimethylsilyl)ethanolHCID 86746722HCID 86746722, compound

Product 1

HCID 86746721HCID 86746721, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 5 mL of a solution containing 1 mmol of the above acid 5, anhydrous dimethylformamide, and 1 mmol of N-methylmorpholine maintained at 0°--5° C., 1 mmol of isobutylchloroformate is added, and the mixture is kept at this temperature for 20 minutes. To this solution is added a solution of 1 mmol of trimethylsilylethanol in 2 mL of anhydrous dimethylformamide (previously cooled to 0°--5° C.), and the solution is stirred for 1 hour at this temperature and allowed to come to room temperature. The solvent is removed in vacuo and the residue is dissolved in 20 mL of ethyl acetate and washed with water. The organic layer is dried and evaporated to give 6.

Workup

  1. temperaturemaintained at 0°--5° C.
  2. temperaturepreviously cooled to 0°--5° C.), and the solution
  3. customto come to room temperature
  4. customThe solvent is removed in vacuo
  5. dissolutionthe residue is dissolved in 20 mL of ethyl acetate
  6. washwashed with water
  7. customThe organic layer is dried
  8. customevaporated
  9. customto give 6

Sources & evidence

ORD record
ord-6e4b095ff327443da0092128174a6435
Source dataset
uspto-grants-1993_04
Patent number
US05202451

Reaction notes

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