Hydroxyamine hydrochloride → HCID 23072375, compound

HRID 1182515Notes

Reaction equation

HRID 1182515 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C:7]([CH2:9][S:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])(=[O:12])=[O:11])=[O:8])=[CH:3][CH:2]=1.[NH2:26][OH:27].Cl>C(N(CC)CC)C>[OH:27][NH:26][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][S:10]([CH2:9][C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:2][CH:3]=1)=[O:8])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 23072460HCID 23072460, compound2×

Product 1

HCID 23072375HCID 23072375, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 14, step 3, but substituting carboxylic acid 228b for 37, and using 1.1 equivalent of NH2OH.HCl and triethylamine each, the title compound 228b was obtained in 52% yield. 1H NMR: (300 MHz, DMSO-d6) δ 10.37 (s, 1H), 8.70 (s, 1H), 8.11 (d, J=8.5 Hz, 2H), 7.86 (d, J=8.5 Hz, 2H), 7.77 (dd, J=1.4 Hz, J=8.5 Hz, 2H), 7.53-7.43 (m, 3H), 5.08 (s, 2H), 3.38-3.25 (t, 2H), 1.99 (t, J=6.6 Hz, 2H), 1.72-1.61 (m, 4H).

Workup

  1. customwas obtained in 52% yield

Sources & evidence

ORD record
ord-892dd8c8613c48bebb5ff6f041567066
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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