Hydroxyamine hydrochloride → HCID 23072368, compound

HRID 1182472Notes

Reaction equation

HRID 1182472 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:7])=[CH:2]1.[NH2:17][OH:18].Cl>C(N(CC)CC)C>[OH:18][NH:17][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]([C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)=[O:7]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 23072364HCID 23072364, compound

Product 1

HCID 23072368HCID 23072368, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 14, step 3, but substituting carboxylic acid 50j for 37 and using 1.1 equivalent of NH2OH.HCl and triethylamine each, the title compound was obtained as light yellow solid in 33% yield: 1H NMR (300 MHz, CD3OD/CDCl3=5/1) δ 8.09 (br s, 1H), 7.46 (m, 1H), 6.75 (m, 1H), 2.76 (t, J=7.5 Hz, 2H), 2.10 (t, J=7.5 Hz, 2H), 1.60-1.72 (m, 4H), 1.36 (m, 4H); 13C NMR (75.4 MHz, CD3OD/CDCl3=5/1) δ 23.90, 24.99, 28.45(2), 32.48, 39.98, 108.19, 127.37, 144.15, 147.43, 171.08, 196.21.

Sources & evidence

ORD record
ord-9895dc2c80204eab9cad440bde5b4ada
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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