Trifluoroacetic acid → HCID 14523424, compound

HRID 2050665Notes

Reaction equation

HRID 2050665 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:15]2[CH2:16][N:17]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[C@@H:10]1[C@H:11]([O:14]2)[O:12]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>O>[CH2:1]([O:8][C@H:9]1[C@H:15]([OH:14])[CH2:16][N:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@@H:10]1[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14523421HCID 14523421, compound

Product 1

HCID 14523424HCID 14523424, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 3-O-benzyl-N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-α-D-lyxofuranoside (14α) (1.015 g, 2.77 mmol) was stirred in a 1:1 mixture of trifluoroacetic acid and water (20 ml). Once all the starting material had dissolved, the solvents were evaporated (without heat) and purification by flash chromatography (ethyl acetate-hexane 1:2) gave 3-O-benzyl-N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-D-lyxose (901 mg, 92%) as a clear oil, [α]20 D -24.2° (c, 1.39 in chloroform); νmax (film) 3400 (OH), 1700 (2×CO), 1425, 1360, 1195 and 700 cm-1 ; δH 2.55 (1H, bs, OH); 3.65 (1H, 2×d, H-5); 3.79 (1H, 2×dd, H-5'); 4.03, 4.31 (2H, 2×bs, H-2, H-3); 4.44, 4.55 (1H, bs and dd, H-4); 4.51-4.71 (2H, m, CH2Ph); 5.09-5.20 (2H, m, CH2 -Z); 7.29-7.40 (10H, m, H-Ph); 9.49, 4.59 (1H, 2×d, H-1, J1,2 0.7 Hz). m/z: 91 (100%), 108 (68%), 230 (50%), 356 (M+H+, 20%). (Found C, 67.76; H, 6.48; N, 3.77. C20H21NO5 requires C, 67.59; H, 5.96; N, 3.94). Methyl 3-O-benzyl-N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-β-D-lyxofuranoside (14β) (976 mg, 2.64 mmol) reacted similarly: it afforded the title compound (15) (820 mg, 87%), spectroscopically identical to that prepared above, under the same reaction conditions.

Workup

  1. dissolutionOnce all the starting material had dissolved
  2. customthe solvents were evaporated
  3. temperature(without heat) and purification by flash chromatography (ethyl acetate-hexane 1:2)

Sources & evidence

ORD record
ord-f79a562ee54e41ab8550d8a8c001c96b
Source dataset
uspto-grants-1991_05
Patent number
US05013842

Reaction notes

Loading…