Lithium tritertbutoxyaluminohydride → HCID 11989984, compound

HRID 1715273Notes

Reaction equation

HRID 1715273 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](Cl)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>COCCOC>[OH:17][CH2:16][C:13]1[S:14][CH:15]=[C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])[N:12]=1

Participants

4

Reactant 2

HCID 16684435Lithium tritertbutoxyaluminohydrideHCID 86621993HCID 86621993, compound

Product 1

HCID 11989984HCID 11989984, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above, (200.5 mg; 0.66 mmol; 1 eq.), is dissolved in DME (7 ml) and is cooled down to −78° C. Lithium tri-tert-butoxyaluminohydride (Aldrich)(2.65 ml; 0.50 M; 1.33 mmol; 2 eq.) is added dropwise. After one hour the reduction is complete. The reaction mixture is poured on ice. The two layers are separated and the organic phase is dried over MgSO4 and concentrated. The resulting product is purified by preparative HPLC, affording Compound (35) as white-off solid (10.5 mg; 6%). 1H NMR (DMSO-d6, 300 MHz) δ 2.12 (s, 3H), 2.45 (s, 3H), 4.75 (s, 2H), 7.61 (s, 1H), 12.08 (s, 1H). M− (ESI): 268.11; M+ (ESI): 270.16. HPLC (method A), Rt: 1.74 min (purity: 100%).

Workup

  1. additionThe reaction mixture is poured on ice
  2. customThe two layers are separated
  3. dry with materialthe organic phase is dried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting product is purified by preparative HPLC

Sources & evidence

ORD record
ord-29a5750709144998bf68c7689ec84d4c
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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