Ammonium Chloride → HCID 86598978, compound

HRID 1816442Notes

Reaction equation

HRID 1816442 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[O:15]CC3C=CC=CC=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[C:24]([O:28][C:29](=[O:36])[NH:30][CH2:31][CH:32]([OH:35])[CH2:33]Cl)([CH3:27])([CH3:26])[CH3:25].CC(C)([O-])C.[Li+].[NH4+].[Cl-]>CN(C=O)C.C1COCC1.O>[S:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH2:33][C@H:32]([CH2:31][NH:30][C:29](=[O:36])[O:28][C:24]([CH3:27])([CH3:26])[CH3:25])[O:35][C:14]3=[O:15])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 17817371HCID 17817371, compoundHCID 22246694HCID 22246694, compoundHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 86598978HCID 86598978, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Step 2 (7.0 g, 21.3 mmol) in DMF (14 mL) is cooled at. 0° C. and treated with (3-chloro-2-hydroxy-propyl)carbamic acid tert-butyl ester (5.6 g, 27 mmol) and then lithium tert-butoxide (51 mL of a 1.0 M solution in THF) dropwise over 15 min. The reaction mixture is stirred for 20 h at room temperature and then treated with 40 mL of satd. NH4Cl and 100 mL of H2O. The solution is extracted with two portions of dichloromethane and the combined organic phases washed with H2O, brine and dried (MgSO4), filtered and concentrated. The crude product is purified by column chromatography (0-50% ethyl acetate-hexanes) to provide the title compound as a foam.

Workup

  1. additiontreated with 40 mL of satd
  2. extractionThe solution is extracted with two portions of dichloromethane
  3. washthe combined organic phases washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography (0-50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-9a77477d654f4ff79ef27fe8c2f9dc44
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

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