HCID 67296515, compound → HCID 68523686, compound

HRID 1189936Notes

Reaction equation

HRID 1189936 reaction equation
[CH2:1]([S:5]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>>[CH2:1]([S:5]([NH:8][C:9]1[CH:10]=[C:11]([C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 67296515HCID 67296515, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 68523686HCID 68523686, compound

Procedure

Oxidation of tert-butyl 3-(3-(butylsulfonamido)phenyl)-3-hydroxypropylcarbamate by PCC following the method used in Example 18 gave tert-butyl 3-(3-(butylsulfonamido)phenyl)-3-oxopropylcarbamate as white solid: Yield (0.18 g, 41%); 1H NMR (400 MHz, CD3OD) δ 8.01-8.04 (m, 1H), 7.82-7.84 (m, 1H), 7.55 (t, J=8.0 Hz, 1H), 7.49-7.52 (m, 1H), 5.86-5.64 (m, 1H), 3.71-3.75 (m, 2H), 3.43 (q, J=6.0 Hz, 2H), 3.21 (t, J=6.8 Hz, 2H), 1.82-1.90 (m, 2H), 1.48-1.58 (m, 2H), 1.41-1.44 (m, 18H), 0.99 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-df87b8fb87a24ee4a6ea84e54f4a8a57
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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