Ammonium Chloride → Carbamic acid, N-(5-iodo-4-methyl-2-thiazolyl)-, 1,1-dimethylethyl ester

HRID 1009031ノート

反応式

HRID 1009031 の反応式
[I:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[CH3:8].[O:9](C(OC(C)(C)C)=O)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=O.C([O-])(O)=O.[Na+].[NH4+].[Cl-]>CC(O)(C)C.CN(C1C=CN=CC=1)C>[C:13]([O:12][C:10](=[O:9])[NH:7][C:5]1[S:6][C:2]([I:1])=[C:3]([CH3:8])[N:4]=1)([CH3:16])([CH3:15])[CH3:14]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 233417955-Iodo-4-methyl-2-thiazolamine

生成物 1

HCID 86630949Carbamic acid, N-(5-iodo-4-methyl-2-thiazolyl)-, 1,1-dimethylethyl ester収率 58.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6386tert-Butanol溶媒

実験手順

The above prepared 5-iodo-4-methyl-thiazol-2-ylamine (2.768 g, 12 mmol) was dissolved in 30 mL of tBuOH and treated successively with BOC2O (3.02 g, 1.2 eq.), DMAP (0.141 g, 0.1 eq.), and NaHCO3 (3.39 g, 3.5 eq.). After stirring for 18 h at ambient temperature, the reaction mixture was poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, hexane/ethyl acetate=8/2), yielded finally 2.383 g of the title compound as off-white foam.

後処理

  1. extractiontwofold extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-d42928a5b8c54e4cb7ba433b660b97a9
出典データセット
uspto-grants-2011_07
特許番号
US07973051B2

反応ノート

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