Benzyl Bromide → HCID 178521679, compound

HRID 1444654Notes

Reaction equation

HRID 1444654 reaction equation
O[C@@H]1CC[C@H](NC(NC23CC4CC(CC(C4)C2)C3)=O)CC1.[CH2:22]([O:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:37]([NH:39][C:40]23[CH2:49][CH:44]4[CH2:45][CH:46]([CH2:48][CH:42]([CH2:43]4)[CH2:41]2)[CH2:47]3)=[O:38])[CH2:32][CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(Br)C1C=CC=CC=1.[H-].[Na+]>>[CH2:22]([O:29][C@@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:37]([NH:39][C:40]23[CH2:47][CH:46]4[CH2:48][CH:42]([CH2:43][CH:44]([CH2:45]4)[CH2:49]2)[CH2:41]3)=[O:38])[CH2:32][CH2:31]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178521677HCID 178521677, compoundHCID 178521680HCID 178521680, compound

Product 1

HCID 178521679HCID 178521679, compoundYield 60%

Procedure

Compound 1078 (2.22 g, 60%) was synthesized from compound 1077 (0.29 g, 1 mmol) by the same method) as that described for compound 1032 with benzyl bromide (0.20 g, 1.2 mmol) and 60% sodium hydride (0.06 g, 1.5 mmol). Yield: 0.35 g (92% of theory). M.P.: 181° C. 1H NMR (300 MHz, CDCl3): δ 7.43-7.24 (m, 5H), 4.49 (s, 2H), 4.11 (d, J=8.3 Hz, 1H), 4.02 (s, 1H), 3.66-3.51 (m, 2H), 2.23-1.07 (m, 23H).

Sources & evidence

ORD record
ord-4fe00149e28b48ee865da33f66a34a25
Source dataset
uspto-grants-2010_02
Patent number
US07662910B2

Reaction notes

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