Trifluoroacetic acid → HCID 57144060, compound

HRID 429912Notes

Reaction equation

HRID 429912 reaction equation
[O:1]=[C:2]1[C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Si:15]([CH2:20]C)([CH2:18]C)[CH2:16]C)[CH:10]=2)[N:6](C(OC(C)(C)C)=O)[C@@H:5]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:4]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:3]1.C(O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl>[O:1]=[C:2]1[C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Si:15]([CH3:16])([CH3:18])[CH3:20])[CH:10]=2)[NH:6][C@@H:5]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C@@H:4]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 86757601HCID 86757601, compound

Product 1

HCID 57144060HCID 57144060, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to example 82, 2.47 g of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-(triethylsilyl)benzyl)-4-morpholinecarboxylate was treated with 4.1 mL of TFA in 40 mL of CH2Cl2 for 3 h. Neutralization with 8 mL of Et3N and work-up in the usual manner gave a thick oil. Purification of the crude material by flash chromatography on 80 g of silica gel (85:15 hexane:EtOAc) afforded 1.70 g (83%) of (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-(trimethylsilyl)benzyl)morpholine as a white crystalline solid, m.p. 94-95° C.

Workup

  1. customgave a thick oil
  2. customPurification of the crude material by flash chromatography on 80 g of silica gel (85:15 hexane:EtOAc)

Sources & evidence

ORD record
ord-1e20e84e2eb44a00bf0c52d01ceb6909
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

Loading…