(6R)-9-fluoro-13,16-dioxa-2,11,20,21,24-pentazapentacyclo[16.5.2.02,6.07,12.021,25]pentacosa-1(24),7(12),8,10,18(25),19,22-heptaen-17-one → (6R)-9-fluoro-14-oxa-2,11,18,19,22-pentazapentacyclo[14.5.2.17,11.02,6.019,23]tetracosa-1(22),7,9,16(23),17,20-hexaene-15,24-dione

HRID 1426928Notes

Reaction equation

HRID 1426928 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[N:23][CH:24]=1)[O:21][CH2:20][CH2:19][O:18][C:17](=[O:25])[C:16]1=[C:26]3[N:27]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1>C(#N)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[O:21])[N:23]([CH:24]=1)[CH2:20][CH2:19][O:18][C:17](=[O:25])[C:16]1=[C:26]3[N:27]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1

Participants

3

Reactant 1

HCID 70168413(6R)-9-fluoro-13,16-dioxa-2,11,20,21,24-pentazapentacyclo[16.5.2.02,6.07,12.021,25]pentacosa-1(24),7(12),8,10,18(25),19,22-heptaen-17-one

Product 1

HCID 70169716(6R)-9-fluoro-14-oxa-2,11,18,19,22-pentazapentacyclo[14.5.2.17,11.02,6.019,23]tetracosa-1(22),7,9,16(23),17,20-hexaene-15,24-dioneYield 9%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Obtained as a by-product of Example 14, Step C, and isolated as a white solid (5 mg, 9% yield) by reverse phase column chromatography (Biotage SP4 system C-18 25+M column, 5 to 60% acetonitrile/water) of the crude material of Example 14, Step C. MS (apci) m/z=370.2 (M+H).

Workup

  1. customObtained as a by-product of Example 14, Step C

Sources & evidence

ORD record
ord-e845aeb7e3164ade9b0ba12c4c9fe881
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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