Hydrochloric Acid → HCID 131717966, compound

HRID 1587151Notes

Reaction equation

HRID 1587151 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:31])[CH2:14][CH2:15][CH:16]3[C@@:21]4([CH3:30])[CH2:22][CH2:23][CH:24]([O:26][C:27](Cl)=[O:28])[CH2:25][C:20]4=[CH:19][CH2:18][CH:17]3[CH:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35].Cl.C(N(CC)CC)C>C(Cl)Cl.CO>[OH:35][CH2:34][CH:33]([NH:32][C:27](=[O:28])[O:26][C@H:24]1[CH2:23][CH2:22][C@@:21]2([CH3:30])[C:20](=[CH:19][CH2:18][C@@H:17]3[C@@H:16]2[CH2:15][CH2:14][C@@:13]2([CH3:31])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:25]1)[CH2:36][OH:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 68294SerinolHCID 54236888C28H45ClO2

Product 1

HCID 131717966HCID 131717966, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.00 g of cholesteryl chloroformate in 20 ml of methylene chloride is added dropwise to a mixture of 1.4 g of DL-serinol.HCl and 3.1 ml of triethylamine in 30 ml of methylene choride. After stirring for 45 hours the mixture is taken up in aqueous methanol and extracted with chloroform. The organic phase is dried and concentrated. After chromatography over SiO2 with chloroform and then with ether there are obtained 4.3 g of cholest-5-en-3β-yl [2-hydroxy-1-(hydroxymethyl)ethyl]carbamate, m.p. 158° C. (decomposition). b) A solution of 3.7 g of the product of a) in 30 ml of methylene chloride, 10 ml of THF and 0.6 ml of pyridine is treated under argon with 1 ml of phenyl chloroformate in 15 ml of methylene chloride. After stirring for 1 hour the solution is taken up in 200 ml of water and 50 ml of 0.1N HCl and extracted with 150 ml of methylene chloride. The organic phase is dried and concentrated. After chromatography over SiO2 with n-hexane/ether (1:1) and ether there are obtained 2.1 g of cholest-5-en-3β-yl [(RS)-2-hydroxy-1-[(phenoxycarbonyl)oxymethyl]ethyl]carbamate.

Workup

  1. extractionextracted with chloroform
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aaaf562cc74b4f6e9aa498846b82186b
Source dataset
uspto-grants-1993_06
Patent number
US05215972

Reaction notes

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