Hydroxylamine → 6-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyhexanamide

HRID 1926191Notes

Reaction equation

[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[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.[NH2:39][OH:40]>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:39][OH:40])=[O:25])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid (335 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 (147 mg, 42%) as a yellow solid. 1H NMR (DMSO-d6) δ1.19 (m, 2H, CH2), 1.30 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.92 (t, J=8.0 Hz, 2H, CH2CO), 3.24 (m, 2H, NCH2), 7.08 (s, 1H, ═CH—CO), 7.28 (m, 2H, Ar—H), 7.41 (m, 2H, Ar—H), 7.76 (m, 1H, Ar—H), 7.81 (m, 2H, Ar—H), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.67 (d, J=8.0 Hz, 1H, Ar—H), 10.32 (s, 1H, NH—O). LC-MS (m/z) 351 (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-4e98b7e59e1f4896962dca486b00dd7f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178577B2

Reaction notes

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