Sodium → HCID 21914852, compound

HRID 1246530Notes

Reaction equation

HRID 1246530 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:26](N(OC)C)=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[Al].[Li].[Na]>C1COCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([CH:26]=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 16211445Aluminum;lithiumHCID 86595608HCID 86595608, compound

Product 1

HCID 21914852HCID 21914852, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of the compound obtained in Step 1 (3.93 g) in THF (80 mL) was added lithium aluminium hydirde (499 mg) slowly (over 15 min) at 5–10° C. (under ice-cooling). The mixture was stirred at 5° C. for 1 h. 30 mL of aquaous solution of sodium pottasium tartrate (1M) was added slowly under ice-cooling, and then the mixture was stirred for another 0.5 h at r.t. The mixture was extracted with ethyl acetate, and the organic layer was dried over MgSO4, and concecntrated in vacuo to give pale yellow oil. This oil was triturated with IPE and EtOAc to give tert-butyl (4-{2-[2-(acetylamino)-5-formyl-1,3-thiazol-4-yl]ethyl}phenyl)carbamate as pale yellow powder (2.67 g).

Workup

  1. temperature(under ice-cooling)
  2. temperaturecooling
  3. stirringthe mixture was stirred for another 0.5 h at r.t
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over MgSO4
  6. customto give pale yellow oil
  7. customThis oil was triturated with IPE and EtOAc

Sources & evidence

ORD record
ord-a4c102456eb2400eb559cd039294289d
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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