Trifluoroacetic acid → HCID 18653190, compound

HRID 1755954Notes

Reaction equation

HRID 1755954 reaction equation
O[C@H:2]([C:22]1[CH:23]=[CH:24][C:25]2[O:30][C@H:29]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:34][CH:33]=3)C=C[C:26]=2[CH:46]=1)[C@H:3]([O:19][CH2:20][CH3:21])C(N1[C@@H](CC2C=CC=CC=2)COC1=O)=O.C([SiH](CC)CC)C.FC(F)(F)[C:56]([OH:58])=[O:57]>>[CH2:39]([O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][CH2:29][O:30][C:25]2[CH:24]=[CH:23][C:22]([CH2:2][C@H:3]([O:19][CH2:20][CH3:21])[C:56]([OH:58])=[O:57])=[CH:46][CH:26]=2)=[CH:33][CH:34]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22851398HCID 22851398, compound

Product 1

HCID 18653190HCID 18653190, compound

Procedure

(R) -6-{(1R, 2S)-1-Hydroxy-2-ethoxy-3-[(S)-4-benzyl-2-oxo-3-oxazolidinyl ]-3 -oxopropyl}-2-(4-benzyloxybenzyl)-2H-benzopyran (18.8 g, 31 mmol) was dissolved in trifluoroacetic acid (200 ml) and triethylsilane (49 ml, 0.31 mmol) was added. After 45 minutes the volatile components were evaporated and the oily residue was triturated with isopropyl alcohol. The product was purified by flash-chromatography (hexanes/ethyl acetate, 2:) and obtained as a thick oil (8.9 g).

Workup

  1. customAfter 45 minutes the volatile components were evaporated
  2. customthe oily residue was triturated with isopropyl alcohol
  3. customThe product was purified by flash-chromatography (hexanes/ethyl acetate, 2:)

Sources & evidence

ORD record
ord-8f1722b4ac4c4c52a4c406574e0047ab
Source dataset
uspto-grants-1995_08
Patent number
US05438074

Reaction notes

Loading…