Boc-Tyr-OMe → HCID 18343037, compound

HRID 2300616Notes

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[S: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][CH2:37]O)[CH3:23]>>[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:37][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)[S:28][C:24]=2[CH2:22][CH3:23])=[CH:18][CH:19]=1)[C:3]([OH:2])=[O:21]

Participants

Reactant 2

HCID 7019130Boc-Tyr-OMe

HCID 18376376HCID 18376376, compound

Product 1

HCID 18343037HCID 18343037, compoundYield 94%

Procedure

Intermediate 56 was prepared as described above for the preparation of intermediate 52. From 534 mg of N-(Boc)-L-Tyrosine methyl ester and 500 mg of Intermediate 11B was prepared 900 mg of BOC-protected intermediate methyl ester (94% yield; 1H NMR (CDCl3, 300 MHz) δ7.9 (dd, 2H, 8.7, 5.2), 7.13 (t, 2H, J=8.6), 7.04 (d, 2H, J=8.5), 6.85 (d, 2H, J=8.6), 4.97 (d, 1H, J=7.9), 4.55 (m, 1H), 4.32 (t, 2H, J=6.8), 3.73 (s, 3H), 3.21 (t, 2H, J=6.7), 3.10-3.02 (m, 2H), 2.89 (q, 2H, J=7.5), 1.44 (s, 9H), 1.36 (t, 3H, J=7.5); From 850 mg of protected intermediate was prepared 900 mg of intermediate 56 as a solid. 1H NMR (DMSO-d6, 300 MHz) δ8.0 (br s, 2H), 7.91-7.87 (m, 2H), 7.30 (dt, 2H, J=8.8, 2.1), 7.14 (d, 2H, J=8.6), 6.90 (d, 2H, J=8.6), 4.27 (t, 2H, J=6.5), 4.12 (m, 1H), 3.11 (t, 2H, J=6.5), 3.0 (m, 2H), 2.86 (q, 2H, J=7.5), 1.26 (t, 3H, J=7.5); low resolution MS (ES+)m/e 414.85 (MH+).

Sources & evidence

ORD record: ord-519380521b3847a2b5d2fefc476fe75f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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