Formaldehyde → HCID 77078276、化合物

HRID 446184ノート

反応式

HRID 446184 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 77078276HCID 77078276、化合物収率 87.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5d0224d951c94dc2bcd6a3e6d10d5b5b
出典データセット
uspto-grants-2013_07
特許番号
US08476451B2

反応ノート

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