tert-Butyl (8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-yl)carbamate → tert-butyl (1E,4E)-8-(4-((3S,4S)-3,4-dihydroxypyrrolidine-1-carbonyl)phenyl)-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate

HRID 38007Notes

Reaction equation

HRID 38007 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:29]=1)[N:7]=[C:8]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][C:10]([C:12](=[O:20])[N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])=[CH:11]2.[OH:30][C@@H:31]1[C@@H:35]([OH:36])[CH2:34][N:33]([C:37]([C:39]2[CH:44]=[CH:43][C:42](B3OC(C)(C)C(C)(C)O3)=[CH:41][CH:40]=2)=[O:38])[CH2:32]1>>[OH:36][C@@H:35]1[C@@H:31]([OH:30])[CH2:32][N:33]([C:37]([C:39]2[CH:40]=[CH:41][C:42]([C:2]3[CH:3]=[CH:4][C:5]4=[C:6]([CH:29]=3)[N:7]=[C:8]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:9][C:10]([C:12](=[O:20])[N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])=[CH:11]4)=[CH:43][CH:44]=2)=[O:38])[CH2:34]1

Participants

3

Reactant 2

HCID 46928349tert-Butyl (8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-yl)carbamateHCID 66960166((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone

Product 1

HCID 86653479tert-butyl (1E,4E)-8-(4-((3S,4S)-3,4-dihydroxypyrrolidine-1-carbonyl)phenyl)-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate

Procedure

The title compound was prepared by the procedure as described in Example 124 (Step F) using tert-butyl (1E,4E)-8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-ylcarbamate and ((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone. MS APCI (+) m/z 591 (M+1) detected

Sources & evidence

ORD record
ord-a92fc6b3d2f1426ab5b6f5f93a8d0cb6
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Reaction notes

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