HCID 86652446, compound → HCID 11998797, compound

HRID 1360890Notes

Reaction equation

HRID 1360890 reaction equation
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:26][CH:25]3[O:27][CH:22]([CH:23]([CH2:28][OH:29])[O:24]3)[CH2:21]2)(=[O:19])=[O:18])=[CH:5][C:6]=1[C:7]1[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=1[CH3:16].C([Li])CCC>C1COCC1>[OH:29][CH2:28][C@H:23]1[C@H:22]2[O:27][C@H:25]([CH2:26][N:20]([S:17]([C:4]3[S:3][CH:2]=[C:6]([C:7]4[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=4[CH3:16])[CH:5]=3)(=[O:18])=[O:19])[CH2:21]2)[O:24]1

Participants

4

Reactant 2

HCID 86652446HCID 86652446, compoundHCID 178418339Butyllithium

Product 1

HCID 11998797HCID 11998797, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-{5-[2-Bromo-5-(7-hydroxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-sulfonyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (450 mg; 0.86 mmol; 1 eq), is dissolved in anhydrous THF (45 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (3.4 ml; 1.6 M; 6.86 mmol; 8 eq) is added dropwise. The reaction is stirred 1 hour and it is quenched with water. Solvents are evaporated and the resulting crude product is purified by preparative HPLC, affording Compound (37) as a white-off solid (74.1 mg; 15%).

Workup

  1. customit is quenched with water
  2. customSolvents are evaporated
  3. customthe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-558442fb4c3c47209ac4887cc1421c11
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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