Methanol → HCID 11795796, compound

HRID 975784Notes

Reaction equation

HRID 975784 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:30][CH2:29][C:11]2([N:15]([CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][N:13]([CH2:23][C:24]([O:26]C)=[O:25])[C:12]2=[O:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].CO>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([CH2:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:14][N:13]([CH2:23][C:24]([OH:26])=[O:25])[C:12]2=[O:28])[CH2:29][CH2:30]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 19660Carbonate IonHCID 10717177HCID 10717177, compound

Product 1

HCID 11795796HCID 11795796, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 4 g (9.45 mmol) of methyl 8-(t-butoxycarbonyl)-1-cyclohexylmethyl-4-keto-1,3,8-triazaspiro [4.5]decan-3-acetate, 4 g (72 mmol) carbonate 60 ml of methanol and 40 ml of water was heated at reflux for 3 hours. The resulting solution was concentrated to about one-half of its original volume and then it was carefully acidified with 2N HCl at 0° C. The resulting mixture was extracted with ethyl acetate. After the extracts were dried over magnesium sulfate, they were concentrated. The residue solid was recrystallized from hexane to give the product as 2.75 g (69.5%) of colorless crystals, mp 148°-149° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe resulting solution was concentrated to about one-half of its original volume
  4. customwas carefully acidified with 2N HCl at 0° C
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. dry with materialAfter the extracts were dried over magnesium sulfate, they
  7. concentrationwere concentrated
  8. customThe residue solid was recrystallized from hexane

Sources & evidence

ORD record
ord-7cd8b26be91b43dea7571394bd35c5e1
Source dataset
uspto-grants-1997_03
Patent number
US05610142

Reaction notes

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