Benzyl isocyanate → HCID 131723736, compound

HRID 1634046Notes

Reaction equation

[NH2:1][C:2]1[CH:37]=[CH:36][C:5]2[NH:6][C:7](=[O:35])[C@H:8]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[N:9]([CH2:12][C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:38]([N:45]=[C:46]=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[CH2:38]([NH:45][C:46](=[O:47])[NH:1][C:2]1[CH:37]=[CH:36][C:5]2[NH:6][C:7](=[O:35])[C@H:8]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[N:9]([CH2:12][C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:10](=[O:11])[C:4]=2[CH:3]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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}-3-phenyl-propionic acid (0.1 mmol, 50mg) in DMF (2.5 mL) was added benzylisocyanate (31 μl 0.25 mmol). The mixture was shaken at 45° C. over night until no starting material was detected by HPLC. Afterwards the solution was concentrated in vacuo. 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}-3-phenyl-propionic acid (20 mg): MS 634 (M−H)−.

Workup

concentrationAfterwards the solution was concentrated in vacuo
customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-181f6c33d4df421daf91fb8f2a13cd36
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506744B1

Reaction notes

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