Boc-Tyr-OMe → HCID 69835491, compound

HRID 2300617Notes

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][CH:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[CH2:35][CH2:36]O)[CH3:23]>>[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:36][CH2:35][C:25]2[N:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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 18376378HCID 18376378, compound

Product 1

HCID 69835491HCID 69835491, compoundYield 94%

Procedure

Intermediate 57 was prepared as described above for the preparation of intermediate 52. From 575 mg of N-(Boc)-L-Tyrosine methyl ester and 500 mg of Intermediate 9B was prepared 940 mg of BOC-protected intermediate methyl ester (94% yield; 1H NMR (DMSO-d6, 300 MHz) δ7.93 (m, 2H), 7.47-7.41 (m, 3H), 7.04 (d, 2H, J=8.4), 6.86 (d, 2H, J=8.6), 4.96 (d, 1H, J=4.56 (m, 1H), 4.34 (t, 2H, J=6.8), 3.73 (s, 3H), 3.23 (t, 2H, J=6.9), 3.04 (m, 2H), 2.90 (q, 2H, J=7.5), 1.44 (s, 9H), 1.37 (t, 3H, J=7.5)); From 900 mg of protected intermediate was prepared 900 mg of intermediate 57 as a solid. 1H NMR (DMSO-d6, 300 MHz) δ8.16 (br s, 2H), 7.85 (m, 2H), 7.5-7.43 (m, 3H), 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), 3.12 (t, 2H, J=6.5), 3.0 (m, 2H), 2.86 (q, 2H, J=7.5), 1.26 (t, 3H, J=7.5).

Sources & evidence

ORD record: ord-78258436c966412ab7265be0151b9f8d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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