Dimethylformamide → HCID 86762272, compound

HRID 476406Notes

Reaction equation

HRID 476406 reaction equation
[C:1](C1SC=CN=1)([O:3][C:4](C)(C)[CH3:5])=[O:2].C(O[C:16]([C:18]1[N:19]=[C:20]([NH:23][C:24]([C:26]2[N:27]=[C:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[S:29][CH:30]=2)=[O:25])[S:21][CH:22]=1)=[O:17])C.C(O)(C(F)(F)F)=O.[S:46]1[CH:50]=[CH:49][N:48]=[CH:47]1.C[N:52](C=O)C>>[CH2:4]([O:3][C:1]([C:49]1[N:48]=[C:47]([NH:52][C:16]([C:18]2[N:19]=[C:20]([NH:23][C:24]([C:26]3[N:27]=[C:28]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[S:29][CH:30]=3)=[O:25])[S:21][CH:22]=2)=[O:17])[S:46][CH:50]=1)=[O:2])[CH3:5]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 9256ThiazoleHCID 189624871,1-Dimethylethyl 2-thiazolecarboxylateHCID 59799091HCID 59799091, compound

Product 1

HCID 86762272HCID 86762272, compoundYield 52%

Procedure

The Boc thiazole dimer (40) (0.281 g, 0.71 mmol) was deprotected using 95% TFA as described in general procedure D. The resulting residue (40′) was dissolved in dry DMF (5 mL) and the Boc protected thiazole acid (37) (0.172 g, 0.71 mmol) was added and reacted as described in general procedure B. This yielded a yellow foam 0.193 g (52%). LCMS (method 1) rt=3.88 min; m/z (ES+) 524 (M+1).

Workup

  1. additionwas added
  2. customreacted

Sources & evidence

ORD record
ord-4b9186a6bdaf4e7f8ce032ada9aa6ae5
Source dataset
uspto-grants-2014_01
Patent number
US08637664B2

Reaction notes

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