Acetic Acid → [(6R,7S)-2-fluoro-6-methyl-9-(2-morpholin-4-yl-ethyl)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

HRID 1348614Notes

Reaction equation

HRID 1348614 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][CH:17]=O)[C:12]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:11]=2[O:10][C@@H:9]1[CH3:24])([CH3:4])([CH3:3])[CH3:2].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(OC(=O)C)C.CCCCCCC>[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:12]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:11]=2[O:10][C@@H:9]1[CH3:24])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 86605287[(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

Product 1

HCID 67076938[(6R,7S)-2-fluoro-6-methyl-9-(2-morpholin-4-yl-ethyl)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl esterYield 75.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

0.10 mg (0.28 mmol) [(6R,7S)-2-Fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester in 4 ml methanol was reacted with 0.036 ml (0.40 mmol) morpholine, 0.07 ml acetic acid and 0.03 g sodium cyanoborohydride at room temperature. Chromatography on silicagel with ethylacetate/heptane 1:1 yielded 0.09 g (73%) [(6R,7S)-2-fluoro-6-methyl-9-(2-morpholin-4-yl-ethyl)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester, MS m/e (%): 424.3 (M+H+, 100).

Sources & evidence

ORD record
ord-7838c5e1e9d344468fc6f0d00c078398
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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