Trifluoroacetic acid → HCID 18343042, compound

HRID 2300622Notes

Reaction equation

HRID 2300622 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][C:32]([F:35])=[CH:31][CH:30]=2)=[N:26][C:25]=1[CH2:36]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][CH2:36][C:25]2[N:26]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=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 18376375HCID 18376375, compound

Product 1

HCID 18343042HCID 18343042, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate 63 was prepared as described above for the preparation of intermediate 52. From 962 mg of N-(Boc)-L-Tyrosine methyl ester and 720 mg of Intermediate 10D was prepared 1.32 g of BOC-protected intermediate methyl ester (81% yield; 1H NMR (CDCl3, 300 MHz) δ8.07-8.03 (m, 2H), 7.19-7.13 (m, 2H), 7.08 (d, 2H, J=8.4), 6.97 (d, 2H, J=8.4), 4.99-4.97 (m, 3H), 4.58-4.57 (m, 1H), 3.74 (s, 3H), 3.09-3.03 (m, 2H), 2.82 (q, 2H. J=7.5), 1.59 (s, 9H), 1.30 (t, 3H, J=7.5); From 1.31 g of BOC-protected ester intermediate was prepared the crude TFA salt of intermediate 63. 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 1.01 g of the title compound; 1H NMR (DMSO-d6, 300 MHz) δ8.01-7.97 (m, 2H), 7.36 (t, 2H, J=9.0), 7.18 (d, 2H, J=8.4), 6.96 (d, 2H, J=8.4), 4.97 (s, 2H), 3.53-3.51 (m, 2H), 3.09-3.04 (m, 2H), 2.84 (q, 2H, J=7.5), 1.22 (t, 3H, J=7.5); low resolution MS (ES+)m/e 384.87 (MH+); TLC Rf=0.44 (4/1, DCM/MeOH).

Workup

  1. customIntermediate 63 was prepared
  2. filtrationThe resulting solids were filtered
  3. customdried

Sources & evidence

ORD record
ord-d029911a9dc94800b9085a3337e856b0
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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