Water → morpholinoethyl E-6-[1,3-dihydro-4-(1-adamantoyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoate

HRID 1723325Notes

Reaction equation

HRID 1723325 reaction equation
[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:27])/[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:17])=[C:9]([O:28][CH3:29])[C:8]([CH3:30])=[C:7]2[C:3]=1[C:4](=[O:31])[O:5][CH2:6]2.[C:32]12([C:42](Cl)=[O:43])[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]3)[CH2:33]1)[CH2:39]2.O>N1C=CC=CC=1>[C:32]12([C:42]([O:1][C:2]3[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:27])/[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:17])=[C:9]([O:28][CH3:29])[C:8]([CH3:30])=[C:7]4[C:3]=3[C:4](=[O:31])[O:5][CH2:6]4)=[O:43])[CH2:39][CH:38]3[CH2:37][CH:36]([CH2:35][CH:34]([CH2:40]3)[CH2:33]1)[CH2:41]2

Participants

5

Reactant 3

HCID 962WaterHCID 989151-Adamantanecarbonyl chlorideHCID 5281078Mycophenolate Mofetil

Product 1

HCID 18611847morpholinoethyl E-6-[1,3-dihydro-4-(1-adamantoyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate (10.0 g) was dissolved in pyridine (50.0 ml) followed by the addition of 1-adamantanecarbonyl chloride (10.0 ml). The mixture was stirred at room temperature for 90 minutes, then poured into water and extracted with ethyl acetate. The organic solution was dried and evaporated to give morpholinoethyl E-6-[1,3-dihydro-4-(1-adamantoyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoate.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic solution was dried
  3. customevaporated

Sources & evidence

ORD record
ord-11aed884a52f468690104a469b1ebfc7
Source dataset
uspto-grants-1989_08
Patent number
US04861776

Reaction notes

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