Boc-Tyr-OMe → HCID 70161236, compound

HRID 2300612Notes

Reaction equation

HRID 2300612 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.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]([CH3:37])=[C:32]([CH2:34][CH2:35]O)[N:33]=2)=[CH:25][CH:24]=1>>[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:35][CH2:34][C:32]2[N:33]=[C:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[S:30][C:31]=2[CH3:37])=[CH:18][CH:19]=1)[C:3]([OH:2])=[O:21]

Participants

3

Reactant 2

HCID 7019130Boc-Tyr-OMeHCID 18376298HCID 18376298, compound

Product 1

HCID 70161236HCID 70161236, compound

Procedure

Intermediate 48 was prepared from 224 mg of N-(Boc)-L-Tyrosine methyl ester and 180 mg of Intermediate 11 to yield 149 mg (51% overall yield) of the title compound as a solid: 1H NMR (DMSO-d6, 400 MHz) δ7.82 (dd, 2H, J=8.6, 5.5), 7.23 (t, 2H, J=8.7), 7.08 (d, 2H, J=8.4), 6.8 (d, 2H, J=8.5), 4.56 (br s, 1H), 4.19 (t, 2H, J=6.5), 3.56 (m, 1H), 3.03 (t, 2H, J=6.6), 2.95 (m, 1H), 2.79 (dd, 1H, J=14.5, 7.5), 2.37 (s, 3H); low resolution MS (ES+)m/e 400.9 (MH+).

Workup

  1. customto yield

Sources & evidence

ORD record
ord-c6d83688f3a642b09c318e09089eb048
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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