Acetic Acid → (2S,3R,4R) 3,4-dihydroxypipecolic acid, monohydrate

HRID 2050674노트

반응식

HRID 2050674 반응식
C([O:8][C@H:9]1[C@H:14]2[CH2:15][CH2:16][N:17](C(OCC3C=CC=CC=3)=O)[C@@H:10]1[C:11]([O:13]2)=[O:12])C1C=CC=CC=1.C(O)(=[O:30])C>O.[Pd]>[OH2:8].[OH:8][C@H:9]1[C@H:14]([OH:13])[CH2:15][CH2:16][NH:17][C@@H:10]1[C:11]([OH:12])=[O:30]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 145234483-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexono-1,4-lactone

생성물 1

HCID 131716888(2S,3R,4R) 3,4-dihydroxypipecolic acid, monohydrate수율 89%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

실험 절차

3-O-Benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexono-1,4-lactone (26) (321 mg, 0.875 mmol) was dissolved in a 2:1 mixture of acetic acid and water (10 ml) and stirred under hydrogen with palladium black (70 mg) for 48 hours. The reaction mixture was filtered through celite, the solvent removed and the product purified by flash chromatography (CMAW) and ion exchange chromatography. Freeze drying afforded (2S,3R,4R) 3,4-dihydroxypipecolic acid, monohydrate (140 mg, 89%) as a white crystalline solid, m.p. 253°-260° C. with decomposition, [α]20D -1.3° (c, 0.54 in water); νmax (KBr disc) 3390, 1595 (CO), 1400, 1080, 1060 and 890 cm-1 ; 1H NMR (D2O) δ 1.48-1.61 (1H, m, 5-H); 1.99 (1H, ddt, H-5', J5,5' 14.4 Hz, J5', 6;5',6';5',4 3.7 Hz); 2.88 (1H, ddd, 6-H, J6,6' 13.0 Hz, J5,6 11.9 Hz); 3.26 (1H, dt, H-6', J5,6' 3.7 Hz); 3.30 (1H, d, 2-H, J2,3 9.2 Hz); 3.52-3.61 (2H, m, H-3, H-4); 13C NMR (D2O) δ 28.33 (t, C-2); 41.13 (t, C-1); 61.51 (d, H-5); 70.24, 71.85 (2×d, C-3,4); 172.43 (s, C-1). m/z: 124 (M-2×H2O-H+, 100%), 98 (M-H2O-CO2H+, 95%), 116 (M-CO2H+, 75%), 162 (M+H+, 67%). (Found C, 40.16; H, 7.10; N, 7.56. C6H11NO4.H2O requires C, 40.22; H, 7.31; N, 7.82).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent removed
  3. customthe product purified by flash chromatography (CMAW) and ion exchange chromatography
  4. customFreeze drying

출처 및 근거

ORD 기록
ord-0025e1aef0a64836aeb64dcf19b0c65a
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013842

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