Triethylamine → Benzyl 2-(4-((((2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetate

HRID 628156Notes

Reaction equation

HRID 628156 reaction equation
[OH:1][CH2:2][C@:3]([OH:20])([CH3:19])[C:4](=[O:18])[C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH:7]([CH3:9])[CH3:8].Cl[S:22]([C:25]1[C:42]([CH3:43])=[CH:41][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])=[CH:27][C:26]=1[CH3:44])(=[O:24])=[O:23].CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:13]([O:12][C:11]([NH:10][C@@H:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4](=[O:18])[C@@:3]([OH:20])([CH3:19])[CH2:2][O:1][S:22]([C:25]1[C:26]([CH3:44])=[CH:27][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:32])=[CH:41][C:42]=1[CH3:43])(=[O:24])=[O:23])=[O:17])([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86715361tert-butyl ((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)carbamateHCID 86715367Benzyl 2-(4-(chlorosulfonyl)-3,5-dimethylphenoxy)acetate

Product 1

HCID 86715366Benzyl 2-(4-((((2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetateYield 34.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Referring to FIG. 37, to a solution of the tert-butyl ((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)carbamate (0.72 g, 2.5 mmol) in DCM (30 mL) were added benzyl 2-(4-(chlorosulfonyl)-3,5-dimethylphenoxy)acetate (1.1 g, 3 mmol), Et3N (0.52 mL, 3.7 mmol) and DMAP (63 mg, 0.5 mmol). The reaction mixture was stirred at room temperature for 7 h (TLC analysis showed some starting material was left). DCM (50 mL) was added and the resulting mixture was washed with HCl solution (1 N, 30 mL) and saturated aqueous NaHCO3 (30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (petroleum ether/EtOAc=10:1) to give product as a white powder (540 mg, 34.8%). LC-MS analysis confirmed the structure.

Workup

  1. waitwas left)
  2. washthe resulting mixture was washed with HCl solution (1 N, 30 mL) and saturated aqueous NaHCO3 (30 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (petroleum ether/EtOAc=10:1)

Sources & evidence

ORD record
ord-e7df232bc7dd4dde8026fa80d1489f8f
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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