Triethylamine → Thiomorpholinecarboxylic acid ethyl ester

HRID 1760425노트

반응식

HRID 1760425 반응식
[C:1]([N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH:9]1C(O)=O)([O:3][C:4](C)(C)[CH3:5])=[O:2].Cl.C(OC(=O)[C@H](CS)N)C.C(N(CC)CC)C.BrC(Br)C>C1COCC1>[CH2:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][S:11][CH2:12][CH2:13]1)=[O:2])[CH3:5]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 112011,1-DibromoethaneHCID 2723617Ethyl cysteinate hydrochlorideHCID 27568314-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid

생성물 1

HCID 53680559Thiomorpholinecarboxylic acid ethyl ester수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Boc-thiomorpholine-3-carboxylic acid can also be substituted for the compound of formula (XXIV) in Reaction Scheme 7 and can be prepared in the following manner: To THF was added cysteine ethyl ester hydrochloride (1.15 g, 6.18 mmol), triethylamine (4.17 mL, 30 mmol) and dibromoethane (2.51 mL, 6.2 mmol). After stirring for 1 hour and refluxing for 16 hours, the solids were removed by filtration. The solvent was removed in vacuo and the residue was chromatographed on silica to give thiomorpholinecarboxylic acid ethyl ester (0.94 g, 87%). The ester (15.3 g, 95 mmol) was dissolved in dioxane/water (1/1) and di-t-butyldicarbonate (24 g, 110 mmol) and LiOH were added. After stirring for 3 hours, the solvent was removed in vacuo and the pH was adjusted to 3 with KHSO3 and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4), and the solvent was removed in vacuo to give 17.4 g (78%) 4-Boc-thiomorpholine-3-carboxylic acid: 1H NMR (CDCl3) δ 1.45 (m, 9), 2.45 (m, 1), 2.71 (m, 1), 2.93 (m, 1), 3.10 (m, 1), 3.29 (m, 1), 4.11 (m, 1), 4.19 (m, 1), 5.20 (m, 1).

후처리

  1. customcan be prepared in the following manner
  2. temperaturerefluxing for 16 hours
  3. customthe solids were removed by filtration
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed on silica

출처 및 근거

ORD 기록
ord-4b1f2b5cbeef47cc9f7f5d916b47b79a
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06841674B2

반응 노트

불러오는 중…