Hydroxylamine → 2-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyacetamide

HRID 1926184Notes

Reaction equation

[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][C:19](O)=[O:20])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:35][OH:36]>[Cl-].[Na+].O.CN(C=O)C>[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][C:19]([NH:35][OH:36])=[O:20])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2-(9H-fluoren-9-ylidene)acetamido)acetic acid (279 mg, 1 mmol), triethylamine (151 mg, 1.5 mmol) and 20 ml of DMF were stirred at 0° C. while ethyl chloroformate (163 mg, 1.5 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then 50% aqueous solution of hydroxylamine (1.32 g, 20 mmol) was added. The mixture was stirred for 3 hours at room temperature, and then diluted with 1000 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (132 mg, 45%) as a yellow solid. LC-MS (m/z) 295 (M+1).

Workup

additionwas added
stirringThe mixture was stirred for 3 hours at room temperature
filtrationThe solids were collected by vacuum filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-d86deddc4a4b4374999f1c35f50b6251
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178577B2

Reaction notes

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