Trifluoromethanesulfonic acid → HCID 86751018, compound

HRID 356754Notes

Reaction equation

HRID 356754 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].N#N.[CH:11]1([NH:17][C:18](=[O:51])[C@H:19]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[NH:20]C([C@]2(NC(=O)C3C=CC=CC=3)CCC3C(=C(OC)C=CC=3)C2)=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CO>[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].[CH:11]1([NH:17][C:18](=[O:51])[C@H:19]([CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH2:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 86753337HCID 86753337, compound

Product 1

HCID 86751018HCID 86751018, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.1 ml (80.74 mmol) of trifluoromethanesulphonic acid were added dropwise under argon and while cooling with ice to a suspension of 7.5 g (13.54 mmol) of N2 -[(S)-2-benzamido-8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carbonyl]-L-phenylalanine cyclohexylamide in 35 ml of methanol. The mixture was stirred at 80° in a bomb tube for 4 hours, then cooled and subsequently concentrated to a volume of ~20 ml. 50 ml of dichloromethane were added while stirring, the suspension was filtered and the filter residue was washed with dichloromethane and dried, 4.48 g (83%) of L-phenylalanine cyclohexylamide trifluoromethanesulphonate being isolated. The filtrate was washed with water, dried over MgSO4 and concentrated. The residue was chromatographed on 350 g of silica gel with ethyl acetate/hexane (2:3), whereupon 4.0 g (87%) of methyl (S)-2-benzamido-8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylate were obtained. [α]D =+144.0° (CHCl3, c=0.2). IR(KBr): 3366w(br.), 3062w, 2998w, 2948w, 1739s, 1647s, 1586m, 1527s, 1468s, 1437m, 1292m, 1259s, 1099m, 1047m, 774w, 713m. (D. Obrecht, Helv. Chim. Acta 1992, 75, 1666).

Workup

  1. temperaturecooled
  2. concentrationsubsequently concentrated to a volume of ~20 ml
  3. addition50 ml of dichloromethane were added
  4. stirringwhile stirring
  5. filtrationthe suspension was filtered
  6. washthe filter residue was washed with dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-7ddfc8ae2d144dbd93b948521b78144d
Source dataset
uspto-grants-1998_11
Patent number
US05837807

Reaction notes

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