Boc-Tyr-OMe → HCID 69836864, compound

HRID 2300618Notes

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][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)[O: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 18376373HCID 18376373, compound

Product 1

HCID 69836864HCID 69836864, compoundYield 88%

Procedure

Intermediate 58 was prepared as described above for the preparation of intermediate 52. From 230 mg of N-(Boc)-L-Tyrosine methyl ester and 200 mg of Intermediate 10B was prepared 350 mg of BOC-protected intermediate methyl ester (88% yield; 1H NMR (DMSO-d6, 300 MHz) δ8.07-8.01 (m, 2H), 7.15 (t, 2H, J=8.7), 7.04 (d, 2H, J=8.5), 6.84 (d, 2H, J=8.5), 4.50 (m, 1H), 4.24 (t, 2H, J=6.5), 3.72 (s, 3H), 3.04-2.99 (m, 2H), 2.77 (q, 2H, J=7.5), 1.44 (s, 9H), 1.33 (t, 3H, J=7.5); From 340 mg of BOC-protected ester intermediate was prepared 350 mg of intermediate 58 as a crude off-white colored solid. 1H NMR (DMSO-d6, 400 MHz) δ8.13 (br s, 2H), 7.91 (dd, 2H, J=8.8, 5.3), 7.3 (t, 2H, J=8.9), 7.10 (d, 2H, J=8.6), 6.85 (d, 2H, J=8.4), 4.13 (t, 2H, J=6.4), 4.08 (m, 1H), 2.98-2.95 (m, 2H), 2.88 (t, 2H, J=6.5), 2.70 (q, 2H, J=7.4), 1.19 (t, 3H, J=7.5); low resolution MS (ES+)m/e 399.13 (MH+).

Sources & evidence

ORD record: ord-86582eaafaa54ca99a433e7b8199e3fe
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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