1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- → HCID 131734846, compound

HRID 1779162Notes

Reaction equation

HRID 1779162 reaction equation
C(OCC[C@:7]([OH:49])([C@@H:11]([C:29](=[O:48])[NH:30][C@H:31]([C:44]([O:46][CH3:47])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]#[C:42][CH3:43])=[CH:35][CH:34]=1)/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:8]([OH:10])=[O:9])(=O)C.[CH2:50]1[CH2:60][CH2:59]N2C(=NCCC2)C[CH2:51]1.Br[CH2:62][N:63]1[C:71](=[O:72])[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[C:64]1=[O:73]>ClCCl>[CH2:40]([O:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][C@H:31]([NH:30][C:29]([C@H:11]([C@@:7]([OH:49])([CH2:7][C:8]([O:10][CH2:62][N:63]2[C:71](=[O:72])[C:70]3[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=3)[C:64]2=[O:73])=[O:9])[C:8]([O:10][CH2:59][CH2:60][CH2:50][CH3:51])=[O:9])/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:48])[C:44]([O:46][CH3:47])=[O:45])=[CH:34][CH:35]=1)[C:41]#[C:42][CH3:43]

Participants

5

Reactant 3

HCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 90060133HCID 90060133, compound

Product 1

HCID 131734846HCID 131734846, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of No. 5317776 (Compound E; 60 mg, 0.08 mmol), DBU (19 μL, 0.126 mmol) and dichloromethane (0.84 mL) was added 2-bromomethyl-isoindole-1,3-dione (30 mg, 0.126 mmol) commercially available from Aldrich (cat. No. 252611). After the mixture was stirred at room temperature for 6 hours, further 2-bromomethyl-isoindole-1,3-dione (10 mg, 0.04 mmol) and DBU (6.3 μL, 0.04 mmol) were added. Then, 4-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl) 1-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (56 mg, 76%) was obtained (ESI (LC/MS positive mode) m/z 873 (M+H); Rt 3.38 min.).

Workup

  1. additionTo a mixture of No

Sources & evidence

ORD record
ord-28157afdae9846a2917b9f6a0df3c3d4
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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