Water → HCID 22856044, compound

HRID 2399580Notes

Reaction equation

HRID 2399580 reaction equation
[NH2:1][CH2:2][CH:3]([OH:22])[CH2:4][C@@H:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][C@H:6]1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[C:23]([O:27][C:28](SC1C=C(C)C=C(C)N=1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C.O>CO>[C:23]([O:27][C:28]([NH:1][CH2:2][CH:3]([OH:22])[CH2:4][C@@H:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][C@H:6]1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15690642HCID 15690642, compoundHCID 22856041HCID 22856041, compound

Product 1

HCID 22856044HCID 22856044, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-amino-1-[(1S*,2R*)-5,5-dimethyl-2-octyloxycyclohexyl]-2-propanol (50 mg), S-t-butyloxycarbonyl-4,6-dimethyl-2-mercaptopyridine (46 mg) and triethylamine (20 ml) in methanol (1.5 ml) was stirred at room temperature for 2 hrs. Water was added to a reaction mixture and the mixture was partitioned between water and ether. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography (using n-hexane:ethylacetate=5:1 as an eluent) gave 3-[(tert-butoxycarbonyl)amino]-1-[(1S*,2R*)-5,5-dimethyl-2-octyloxycyclohexyl]-2-propanol (55 mg, y. 83%); EI-MS: m/z 395 (M+ -H2O).

Workup

  1. customthe mixture was partitioned between water and ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by silica gel chromatography (

Sources & evidence

ORD record
ord-b11e69869d9b497f8588f709aec5f841
Source dataset
uspto-grants-1995_09
Patent number
US05449785

Reaction notes

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