1-Naphthaleneboronic acid → HCID 54263811, compound

HRID 369201Notes

Reaction equation

HRID 369201 reaction equation
[SH:1][CH2:2][CH:3]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:4]([NH:6][C@H:7]([C:20]([OH:22])=[O:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12](C2SC=CC=2)=[CH:11][CH:10]=1)=[O:5].[C:30]1(B(O)O)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[SH:1][CH2:2][CH:3]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:4]([NH:6][C@H:7]([C:20]([OH:22])=[O:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)=[CH:11][CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 2545321-Naphthaleneboronic acidHCID 516892Sodium BicarbonateHCID 54348658HCID 54348658, compound

Product 1

HCID 54263811HCID 54263811, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The operation is carried out as in Stage 1 of Example 10 starting with methyl ester of N-[(1,1-dimethylethoxy) carbonyl]-O-[(trifluoromethyl) sulphonyl]-L-tyrosine (prepared as indicated in Stage 1 of Example 10), 10 ml of toluene, 282 mg of naphthalene boronic acid and 169.7 mg of sodium bicarbonate, the solution is agitated for 15 minutes, then 94.77 mg of 5-tetrakis (triphenylphosphine) is added. In this way 165.7 mg of expected product is obtained.

Sources & evidence

ORD record
ord-04f9233ca35a4d5a8bdd161add6d8a95
Source dataset
uspto-grants-2000_10
Patent number
US06136842

Reaction notes

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