Methanol → HCID 15673229, compound

HRID 1196460Notes

Reaction equation

HRID 1196460 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C@@H:10]([OH:21])[CH2:11][S:12]([CH2:15][C:16](OCC)=[O:17])(=[O:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(Cl)(Cl)Cl.CO>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1)[C@@H:10]([OH:21])[CH2:11][S:12]([CH2:15][C:16]([NH:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[O:17])(=[O:14])=[O:13])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 4082852-MorpholinoethylamineHCID 15673227HCID 15673227, compound

Product 1

HCID 15673229HCID 15673229, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.98 g (4.7 mmole) of ethyl 2-[[(2R,3S) 3-(t butoxycarbonylamino)-4-cyclohexyl-2-hydroxy-1-butyl]sulfonyl]acetate and 2.3 ml of 4-(2-aminoethyl)morpholine was stirred under N2 at room temperature for 2 days. The light amber syrup was dissolved in 75 ml of ethyl acetate and washed with 3×30 ml of saturated aqueous NH4Cl followed by 30 ml of H2O. The ethyl acetate fraction was dried over Na2SO4, filtered, and concentrated. Further drying in vacuo (oil pump) gave 2.19 g (92%) of a nearly colorless, stiff foam or glass. Structure and purity were confirmed by 300 MHz NMR (CDCl3), mass spectrum, and TLC (9:1 CHCl3 --MeOH).

Workup

  1. washwashed with 3×30 ml of saturated aqueous NH4Cl
  2. dry with materialThe ethyl acetate fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customFurther drying in vacuo (oil pump)
  6. customgave 2.19 g (92%) of a nearly colorless, stiff foam or glass

Sources & evidence

ORD record
ord-436a1ac782334a90ae2a9f1748f881c3
Source dataset
uspto-grants-1992_05
Patent number
US05114925

Reaction notes

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