(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate → ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-formylbiphenyl-4-yl)propionate

HRID 271850Notes

Reaction equation

HRID 271850 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24](NCC(OC(C)(C)C)=O)[CH:23]=2)=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:37]([O:41]C(N[C@@H](CC1C=CC(OS(C(F)(F)F)(=O)=O)=CC=1)C(OCC)=O)=O)(C)(C)C>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH:37]=[O:41])[CH:23]=2)=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 10789275(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoateHCID 86601620ethyl (S)-2-tert-butoxycarbonylamino-3-[3'-(tert-butoxycarbonylmethylamino)biphenyl-4-yl]propionate

Product 1

HCID 86601619ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-formylbiphenyl-4-yl)propionateYield 61%

Procedure

In a manner similar to the preparation of ethyl (S)-2-tert-butoxycarbonylamino-3-[3′-(tert-butoxycarbonylmethylamino)biphenyl-4-yl]propionate (Example 1e), using 173 g (391 mmol) of ethyl (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl)propionate and 82 g (547 mmol) of 3-boronic acid-benzaldehyde, 95.7 g of coupled product are isolated with a 61% yield.

Workup

  1. customare isolated with a 61% yield

Sources & evidence

ORD record
ord-0b6284b7b8124675a23fce52b9388142
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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