Trifluoroacetic acid → HCID 69835826, compound

HRID 2300620Notes

Reaction equation

HRID 2300620 reaction equation
C[O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[CH2:22]([C:24]1[O:28][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[CH2:35]O)[CH3:23].C(O)(C(F)(F)F)=O.[OH-].[Na+]>O>[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:35][C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:28][C:24]=2[CH2:22][CH3:23])=[CH:18][CH:19]=1)[C:3]([OH:2])=[O:21]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 14798Sodium HydroxideHCID 7019130Boc-Tyr-OMeHCID 18376355HCID 18376355, compound

Product 1

HCID 69835826HCID 69835826, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate 61 was prepared as described above for the preparation of intermediate 52. From 465 mg of N-(Boc)-L-Tyrosine methyl ester and 320 mg of Intermediate 8G was prepared 520 mg of BOC-protected intermediate methyl ester (69% yield; 1H NMR (CDCl3, 300 MHz) δ8.09-8.06 (m, 2H), 7.47-7.46 (m, 3H), 7.08 (d, 2H, J=8.7), 6.97 (d, 2H, J=8.7), 5.02 (s, 2H), 5.01 (s, 1H), 4.59-4.55 (m, 1H), 3.74 (s, 3H), 3.08-3.02 (m, 2H), 2.83 (q, 2H, J=7.5), 1.45 (s, 9H), 1.32 (t, 3H, J=7.5); From 510 mg of BOC-protected ester intermediate was prepared the crude TFA salt of intermediate 61. The TFA salt was suspended into water and the pH adjusted to ˜7.0 with 10% NaOH. The resulting solids were filtered and dried to yield 315 mg of intermediate 61; 1H NMR (DMSO-d6, 300 MHz) δ7.96-7.94 (m, 2H), 7.52-7.51 (m, 3H), 7.18 (d, 2H, J=8.4), 6.95 (d, 2H, J=8.4), 4.97 (s, 3H), 3.10-3.05 (m, 1H), 2.86-2.79 (m, 4H), 1.22 (t, 3H, J=7.5); low resolution MS (ES+)m/e 366.86 (MH+); TLC Rf=0.52 (4/1, DCM/MeOH).

Workup

  1. filtrationThe resulting solids were filtered
  2. customdried

Sources & evidence

ORD record
ord-4b7f8884d6bb4f72a37bdba344ac477a
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

Loading…