Formaldehyde → HCID 77078276, 화합물

HRID 446184노트

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HRID 446184 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C@H:11]([OH:24])[CH2:12][C@@H:13]([NH:17][S@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH:14]([CH3:16])[CH3:15])[S:9][CH:10]=1)=[O:5])[CH3:2].[CH2:25]=O>C1(C)C=CC=CC=1>[CH3:2][CH2:1][O:3][C:4]([C:6]1[N:7]=[C:8]([C@@H:11]2[O:24][CH2:25][N:17]([S:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])[CH:13]([CH:14]([CH3:15])[CH3:16])[CH2:12]2)[S:9][CH:10]=1)=[O:5]

참가 물질

4

반응물 2

HCID 712FormaldehydeHCID 24906124ethyl 2-((1R,3R)-3-(N-sulfinyl)amino-1-hydroxy-4-methylpentyl)thiazole-4-carboxylate

생성물 1

HCID 77078276HCID 77078276, 화합물수율 87.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A 0.1 M solution of N-sulfinyl amino alcohol 32 (0.575 g, 1.53 mmol) in toluene (15.3 mL) with paraformaldehyde (0.917 g, 30.5 mmol) was heated in a sealed vessel at 70° C. with stirring for 50 h. After cooling to rt, the mixture was filtered through Celite, washing the filter cake thoroughly with toluene. The solution was concentrated and purified via HPFC (88:12 to 30:70 CH2Cl2:EtOAc) to afford 0.518 g of tetrahydrooxazine 33 (87%) as a foamy yellow solid. [α]25D=+108.4 (c=1.0, CHCl3). IR (film): 1011, 1076, 1087, 1163, 1195, 1474, 1729, 2957, 2979 cm−1. 1H NMR (500 MHz, CDCl3): δ 1.01 (d, 3H, J=6.8 Hz), 1.02 (d, 3H, J=6.8 Hz), 1.17 (s, 9H), 1.35 (t, 3H, J=7.1 Hz), 2.08-2.16 (m, 1H), 2.28-2.40 (m, 1H), 2.31 (d, 1H, J=14.3 Hz), 3.02 (dd, 1H, J=4.7, 10.1 Hz), 4.37 (q, 2H, J=7.1 Hz), 4.72 (d, 1H, J=11.6 Hz), 5.14 (d, 1H, J=11.6 Hz), 5.20 (dd, 1H, J=2.5, 11.5 Hz), 8.11 (s, 1H). 13C NMR (125 MHz, CDCl3): δ 14.3, 20.5, 20.7, 22.8, 27.5, 32.6, 59.2, 61.3, 62.7, 71.4, 71.6, 127.8, 146.5, 161.3, 173.3. HRMS (FAB) calcd. for C17H29N2O4S2 (M+H): 389.1569. Found 389.1566.

후처리

  1. filtrationthe mixture was filtered through Celite
  2. washwashing the filter cake thoroughly with toluene
  3. concentrationThe solution was concentrated
  4. custompurified via HPFC (88:12 to 30:70 CH2Cl2:EtOAc)

출처 및 근거

ORD 기록
ord-5d0224d951c94dc2bcd6a3e6d10d5b5b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476451B2

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