Benzyl isocyanate → HCID 131723739, compound

HRID 1634048Notes

Reaction equation

[NH2:1][C:2]1[CH:32]=[CH:31][C:5]2[NH:6][C:7](=[O:30])[C@H:8]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:33]([N:40]=[C:41]=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C>[CH2:33]([NH:40][C:41](=[O:42])[NH:1][C:2]1[CH:32]=[CH:31][C:5]2[NH:6][C:7](=[O:30])[C@H:8]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:10](=[O:11])[C:4]=2[CH:3]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 3-(R,S)-{2-[7-Amino-3-(S)-(4-hydroxy-benzyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetylamino}-butyric acid (0.2 mmol, 88mg). in DMF (6 ml) was added benzylisocyanate (158 μl 1.2 mmol). The mixture was shaken at 45° C. over night and then was evaporated to dryness. The crude product was purified by RP-HPLC to give 3-(R,S)-{2-[7-(3-benzyl-ureido)-3-(S)-(4-hydroxy-benzyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetylamino}-butyric acid: MS (ISN) 572 (M−H)−.

Workup

customwas evaporated to dryness
customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-114e96b468344c83b171803c4523c71b
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506744B1

Reaction notes

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