Diisopropylethylamine → (R)-N-hydroxy-3-phenyl-2-(4-propoxy-benzenesulfonylamino)-propionamide

HRID 1662971Notes

Reaction equation

HRID 1662971 reaction equation
[NH2:1][C@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([NH:5][OH:6])=[O:4].[CH2:14]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1)[CH2:15][CH3:16].C(N(C(C)C)C(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[OH:6][NH:5][C:3](=[O:4])[C@H:2]([NH:1][S:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:14][CH2:15][CH3:16])=[CH:23][CH:22]=1)(=[O:26])=[O:25])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 10899270(R)-2-Amino-N-hydroxy-3-phenyl-propionamideHCID 122391964-Propoxybenzene-1-sulfonyl chloride

Product 1

HCID 86624467(R)-N-hydroxy-3-phenyl-2-(4-propoxy-benzenesulfonylamino)-propionamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 400 mg (˜0.33 mmol) resin from stage 1.1 are added successively dry dichloromethane (2 ml), 4-dimethylaminopyridine (4 mg, 0.033 mmol), 4-propoxy-benzenesulfonyl chloride (309.8 mg, 1.32 mmol) dissolved in dry dichloromethane (1 ml), and N-ethyldiisopropylamine (0.28 ml, 1.64 mmol). After shaking for 15 h at r.t. the suspension is filtered and the resin washed with dichloromethane (3×), alternating with DMA and H2O (2×), 0.2M aqueous citric acid, alternating with DMA and H2O (2×), alternating with 2-propanol and THF (3×), and with dichloromethane (4×). The resin is dried under reduced pressure to provide polymer-bound (R)—N-hydroxy-3-phenyl-2-(4-propoxy-benzenesulfonylamino)-propionamide.

Workup

  1. filtrationis filtered
  2. washthe resin washed with dichloromethane (3×)
  3. customThe resin is dried under reduced pressure

Sources & evidence

ORD record
ord-da06a340d28c4011a78c88a196146a9d
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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