3-Amino-2,2-dimethylpropanamide → tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate

HRID 660398Notes

Reaction equation

[CH:1]([C@H:4]1[C:8](=[O:9])[O:7][C@H:6]([C@@H:10]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:11][C@H:12]([CH2:16][C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[N:22][N:23]3[CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=2)[CH:13]([CH3:15])[CH3:14])[CH2:5]1)([CH3:3])[CH3:2].OC1C=CC=CN=1.[NH2:46][CH2:47][C:48]([CH3:53])([CH3:52])[C:49]([NH2:51])=[O:50]>CCN(CC)CC>[NH2:51][C:49](=[O:50])[C:48]([CH3:53])([CH3:52])[CH2:47][NH:46][C:8]([C@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][C@H:6]([OH:7])[C@@H:10]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:11][C@H:12]([CH2:16][C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[N:22][N:23]2[CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=1)[CH:13]([CH3:14])[CH3:15])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-4-methylpentylcarbamate (120 mg, 0.25 mmol), Et3N (1.5 mL), 2-hydroxypyridine (71.3 mg, 0.75 mmol), and 3-amino-2,2-dimethylpropanamide (87 mg, 0.75 mmol) was stirred at 80° C. overnight. The mixture was evaporated and purified by flash chromatography on silica gel to give tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-2,9-dimethyldecan-5-ylcarbamate (120 mg, 65%). MS: 646 (M++1)

Workup

customThe mixture was evaporated
custompurified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-17e72e1d922445229db29765fde8dc0c
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084485B2

Reaction notes

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