HCID 44609103, compound → (R)-N-Hydroxy-3-(4-hydroxy-phenyl)-2-[(3-methyl-butyl)-(naphthalene-2-sulfonyl)-amino]-propionamide

HRID 77328Notes

Reaction equation

HRID 77328 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([N:21]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[S:22]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)(=[O:24])=[O:23])[C:17]([NH:19][OH:20])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:20][NH:19][C:17](=[O:18])[C@H:16]([N:21]([CH2:35][CH2:36][CH:37]([CH3:38])[CH3:39])[S:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)(=[O:24])=[O:23])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 44609103HCID 44609103, compound

Product 1

HCID 44609099(R)-N-Hydroxy-3-(4-hydroxy-phenyl)-2-[(3-methyl-butyl)-(naphthalene-2-sulfonyl)-amino]-propionamideYield 20.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-3-(4-benzyloxy-phenyl)-N-hydroxy-2-[(3-methyl-butyl)-(naphthalene-2-sulfonyl)-amino]-propionamide (230 mg, 0.42 mmol) and 200 mg of 10% Pd/C in ethyl acetate (20 mL) are hydrogenated under 50 PSI for 6 h. The reaction mixture is filtered through celite, and concentrated in vacuo. Purification by flash chromatography yields 40 mg of product. 1HNMR (400 MHz, MeOD): δ 0.90 (d, 6H, J=5.5 Hz), 1.5-1.7 (m, 4H), 2.4-2.5 (dd, 1H, J=5 Hz), 3.05-3.15 (dd, 1H, J=5 Hz), 3.35-3.45 (m, 1H), 3.6-3.75 (m, 1H), 4.30-4.40 (q, 1H, J=5 Hz), 6.55 (d, 2H, J=8 Hz), 6.80 (d, 2H, J=8 Hz), 7.7-7.85 (m, 3H), 7.92-8.10 (m, 3H), 8.45 (s, 1H). LCMS (m/z): 457 (M+1). Analytics calculated for C24H28N2O54S: C, 63.14; H, 6.18; N, 6.14. Found: C, 63.03; H, 6.30; N, 5.89.

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-df2d1b683c07492f80b5d73f1024dcce
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Reaction notes

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