(1R,3S,4S)-2-(tert-Butoxycarbonyl)-2-azabicyclo(2.2.1)heptane-3-carboxylic acid → (1R,3S,4S)-3-(2-(2-(2-(((1R,3S,4S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carbonyl)oxy)acetyl)naphtho[1,2-b]thiophen-7-yl)-2-oxoethyl) 2-tert-butyl 2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate

HRID 1521802Notes

Reaction equation

HRID 1521802 reaction equation
[S:1]1[C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][C:3]2[CH:10]=[CH:11][C:12]3[C:17]([C:2]1=2)=[CH:16][CH:15]=[C:14]([C:18](=[O:21])[CH2:19]Br)[CH:13]=3.[C:22]([O:26][C:27]([N:29]1[C@H:34]([C:35]([OH:37])=[O:36])[C@@H:33]2[CH2:38][C@H:30]1[CH2:31][CH2:32]2)=[O:28])([CH3:25])([CH3:24])[CH3:23]>>[C@H:30]12[CH2:38][C@H:33]([CH2:32][CH2:31]1)[C@@H:34]([C:35]([O:37][CH2:19][C:18]([C:14]1[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=1)[C:2]1[S:1][C:5]([C:6](=[O:9])[CH2:7][O:37][C:35]([C@@H:34]4[C@@H:33]5[CH2:38][C@@H:30]([CH2:31][CH2:32]5)[N:29]4[C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])=[O:36])=[CH:4][C:3]=1[CH:10]=[CH:11]3)=[O:21])=[O:36])[N:29]2[C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28]

Participants

3

Reactant 2

HCID 18396216(1R,3S,4S)-2-(tert-Butoxycarbonyl)-2-azabicyclo(2.2.1)heptane-3-carboxylic acidHCID 897518511,1'-(Naphtho[1,2-b]thiophene-2,7-diyl)bis(2-bromoethanone)

Product 1

HCID 117778314(1R,3S,4S)-3-(2-(2-(2-(((1R,3S,4S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carbonyl)oxy)acetyl)naphtho[1,2-b]thiophen-7-yl)-2-oxoethyl) 2-tert-butyl 2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate

Procedure

was synthesized from 1,1′-(naphtho[1,2-b]thiophene-2,7-diyl)bis(2-bromoethanone) (10c) and (1R,3S,4S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (see, e.g., WO 2012/041227) by following an analogous procedure described in Step 5, Example 1. m/z 746.3 (M+H)+.

Sources & evidence

ORD record
ord-e34d5a9f01d9474d977ae7938a127f99
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

Loading…