Iodine → tert-butyl N-[4-(iodomethyl)-4,5-dihydro-1,3-thiazol-2-yl]carbamate

HRID 1280680ノート

反応式

HRID 1280680 の反応式
C(=O)(O)[O-].[Na+].[CH2:6]([S:9][C:10](=[N:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH:11]C(OC(C)(C)C)=O)[CH:7]=[CH2:8].[I:27]I.O>ClCCl>[I:27][CH2:8][CH:7]1[CH2:6][S:9][C:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:11]1

参加物

6

反応物 4

HCID 807IodineHCID 962WaterHCID 516892Sodium Bicarbonate2 回HCID 73994466Tert-butyl allylsulfanyl-[(tert-butoxycarbonyl)amino]methylidenecarbamate

生成物 1

HCID 22747901tert-butyl N-[4-(iodomethyl)-4,5-dihydro-1,3-thiazol-2-yl]carbamate収率 74.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

17 g of sodium bicarbonate are added, at a temperature in the region of 20° C., to a suspension of 25.4 g of tert-butyl allylsulphanyl-[(tert-butoxycarbonyl)amino]methylidenecarbamate in 650 cm3 of dichloromethane, followed by addition of a solution of 24.4 g of iodine predissolved in 850 cm3 of dichloromethane. After 72 hours at a temperature in the region of 20° C., 500 cm3 of water and 500 cm3 of saturated sodium bicarbonate solution are added to the reaction medium and the resulting mixture is then extracted with twice 1 dm3 of ethyl acetate. The organic phases are washed with saturated sodium sulphite solution and then with saturated sodium chloride solution, dried over magnesium sulphate, filtered and then concentrated under reduced pressure (1 kPa) at a temperature in the region of 50° C. The residue obtained is crystallized from ethyl acetate. 20.5 g of tert-butyl N-[(4RS)-4-(iodomethyl)-4,5-dihydro-2-thiazolyl]carbamate are obtained in the form of a yellow solid [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 1.41 (s: 9H); 2.97 (dd, J=11.5 and 7 Hz: 1H); from 3.30 to 3.50 (mt: 3H); 4.12 (mt: 1H); 9.89 (unresolved complex: 1H)].

後処理

  1. extractionthe resulting mixture is then extracted with twice 1 dm3 of ethyl acetate
  2. washThe organic phases are washed with saturated sodium sulphite solution
  3. dry with materialwith saturated sodium chloride solution, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure (1 kPa) at a temperature in the region of 50° C
  6. customThe residue obtained
  7. customis crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-9b535cb7747a4364864e73e430625dfb
出典データセット
uspto-grants-2002_09
特許番号
US06451821B1

反応ノート

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