Ethyl 6-bromohexanoate → HCID 66818671, compound

HRID 1024756Notes

Reaction equation

HRID 1024756 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:34]([O:36][C:37](=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]Br)[CH3:35]>>[CH2:34]([O:36][C:37](=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][O:22][C:20]1[CH:19]=[C:18]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[CH:17]=[C:16]([C:15](=[O:32])[NH:14][CH:11]2[CH2:12][CH2:13][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:33])[CH2:9][CH2:10]2)[CH:21]=1)[CH3:35]

Participants

3

Reactant 2

HCID 117544Ethyl 6-bromohexanoateHCID 66818660HCID 66818660, compound

Product 1

HCID 66818671HCID 66818671, compoundYield 86%

Procedure

Using 0.84 g (1.86 mmol) of {4-[3-(4-cyanophenoxy)-5-hydroxybenzoylamino]cyclohexyl}carbamic acid tert-butyl ester and 6-bromo-hexaanoic acid ethyl ester (0.41 g, 1.86 mmol) and following the procedure of Example 42(b) afforded 0.95 g of the required product. 1H NMR (DMSO-d6): δ 1.15 (3H, t), 1.25 (2H, m), 1.4 (9H, s), 1.45 (3H, m), 1.6 (2H, m) 1.7 (2H, m), 1.8 (4H, m), 2.3 (2H, t), 3.2 (1H, m), 3.7 (1H, m), 4.05 (4H, m), 6.72 (1H, d), 6.88 (1H, s), 7.12 (3H, m), 7.3 (1H, s), 7.84 (2H, d), 8.24 (1H, d).

Sources & evidence

ORD record
ord-fc66b7c2d13347e093ee0af5d3ee0df4
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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