(2S,3R,4S)-2-[(tert-Butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane → HCID 5288373, compound

HRID 973494Notes

Reaction equation

HRID 973494 reaction equation
C(OC([NH:8][C@H:9]([C@@H:17]([OH:24])[C@@H:18]([OH:23])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][C@H:9]([C@@H:17]([OH:24])[C@@H:18]([OH:23])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 9974740(2S,3R,4S)-2-[(tert-Butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Product 1

HCID 5288373HCID 5288373, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

(2S,3R,4S)-2-[(tert-Butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (10.00 g, 29.11 mmol, Luly et al., J. Org. Chem. 1988, 53, 6109) was stirred for 1 h in 4M HCl/dioxane. The solvent was evaporated and the residue was dissolved in water which was washed with ether and then made basic with solid K2CO3. The mixture was saturated with solid NaCl and extracted into chloroform which was dried over Na2SO4 and evaporated to afford 7.09 g (100%) of a white solid, m.p. 110°-111° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water which
  3. washwas washed with ether
  4. extractionextracted into chloroform which
  5. dry with materialwas dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-46995d6cb52b471da4f683a4b5b41a61
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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