tert-Butyl bromoacetate → HCID 5276016, compound

HRID 1788443Notes

Reaction equation

HRID 1788443 reaction equation
[Cl:1][C:2]1[CH:46]=[CH:45][C:5]([C:6]2[C:11]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:22]5[N:26]([CH:27]6[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]6)[C:25]6[CH:33]=[CH:34][C:35]([C:37]([OH:39])=[O:38])=[CH:36][C:24]=6[N:23]=5)[CH:18]=4)[N:13]=3)=[CH:10][C:9]([O:40][CH2:41][CH2:42][O:43]C)=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.BrCC(OC(C)(C)C)=[O:50].BrCCOC>>[C:42]([CH2:41][O:40][C:9]1[CH:10]=[C:11]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22]4[N:26]([CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]5)[C:25]5[CH:33]=[CH:34][C:35]([C:37]([OH:39])=[O:38])=[CH:36][C:24]=5[N:23]=4)[CH:18]=3)[N:13]=2)[C:6]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:46][CH:45]=2)=[CH:7][CH:8]=1)([OH:50])=[O:43]

Participants

4

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 809722-Bromoethyl methyl etherHCID 5276094HCID 5276094, compound

Product 1

HCID 5276016HCID 5276016, compound

Procedure

The title compound was synthesized as described for Compound 475, except tert-butyl bromoacetate was used for alkylation instead of 1-bromo-2-methoxy ethane. The tert-butyl group was removed in a separate step before saponification by a 1 h treatment with TFA.

Workup

  1. customThe tert-butyl group was removed in a separate step before saponification by a 1 h treatment with TFA

Sources & evidence

ORD record
ord-e80f65a9c90345988fb63d7efb2f68f4
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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