Benzoyl chloride → HCID 58982138, compound

HRID 1182494Notes

Reaction equation

HRID 1182494 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)C(Cl)=O.C(Cl)(=O)C1C=CC=CC=1.Br[C:21]1[CH:39]=[CH:38][C:24]([C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=O)=[O:26])=[CH:23][CH:22]=1.C(CCCCCCC(OCC)=O)(=O)C1C=CC=CC=1.[NH2:59][OH:60].Cl>C(N(CC)CC)C>[OH:60][NH:59][C:33](=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:25]([C:24]1[CH:38]=[C:39]([C:10]2[CH:9]=[CH:8][CH:4]=[CH:3][CH:2]=2)[CH:21]=[CH:22][CH:23]=1)=[O:26]

Participants

7

Reactant 5

HCID 7412Benzoyl chlorideHCID 74377Benzoyl chloride, 3-bromo-HCID 443297Hydroxyamine hydrochlorideHCID 10934282Ethyl 8-oxo-8-phenyloctanoateHCID 11024292ETHYL 8-(4-BROMOPHENYL)-8-OXOOCTANOATE

Product 1

HCID 58982138HCID 58982138, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 18, step 1, 2, but substituting respectively 3-bromobenzoyl chloride for benzoyl chloride, the resulting ester was substituted for 49d in Example 67, step 1. Then, following the procedure described in Example 18, step 3, but substituting the final ester for ester 49a, the resulting acid was substituted in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 131 in 35% yield. 1H NMR (300 MHz, CDCl3): δ 8.13 (s, 1H), 7.88-7.30 (m, 8H), 2.96 (br t, 2H), 2.17 (m, 2H), 1.77-1.58 (m, 4H), 1.35 (m, 4H). 13C NMR (75 MHz, CDCl3) δ623.93, 25.12, 28.71(2), 32.73, 38.48, 126.61, 126.88, 127.08, 127.72, 128.85, 128.99, 131.58, 137.30, 140.06, 141.57, 171.82, 200.75.

Sources & evidence

ORD record
ord-29d2ab9e06184fec8090fe2e5950ff90
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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