4-(4-Bromophenyl)butyric Acid → tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylsulfonyl)benzylcarbamate

HRID 735519Notes

Reaction equation

HRID 735519 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[C:16]([C:25]#[N:26])[CH:15]=2)=[O:12])=[CH:4][CH:3]=1.NC1C=CC(S(CC)(=O)=O)=C(C=1)CN[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38].BrC1C=CC(CCCC(O)=O)=CC=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:21])=[O:22])=[C:16]([CH:15]=2)[CH2:25][NH:26][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2527324-(4-Bromophenyl)butyric AcidHCID 57842618HCID 57842618, compoundHCID 578426674-(4-Bromophenyl)-N-(3-cyano-4-(ethylsulfonyl)phenyl)butanamide

Product 1

HCID 57842758tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylsulfonyl)benzylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using a procedure analogous to that used to prepare 6C, except that pyridine was used in place of triethylamine, 15A (0.314 g, 1.00 mmol) was coupled to 4-(4-bromophenyl)butyric acid to give 15B (0.540 g, 100%) as a white foam. 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.31 (m, 3 H) 1.41 (s, 9 H) 1.97-2.08 (m, 2 H) 2.37(t, J=7.47 Hz, 2 H) 2.59-2.70(m, 2 H) 3.11-3.23 (m, 2 H) 4.12(q, J=7.03 Hz, 1 H) 4.50 (d, J=6.15 Hz, 2 H) 5.60 (t, J=5.93 Hz, 1 H) 7.06 (d, J=8.35 Hz, 2 H) 7.39 (d, J=8.35 Hz, 2 H) 7.45-7.50 (m, 1 H) 7.83-7.95 (m, 2 H).

Sources & evidence

ORD record
ord-29efd4da394c44aebc3cc4682e7275b2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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