(4-Methoxyphenyl)boronic acid → HCID 53688502, compound

HRID 369202Notes

Reaction equation

HRID 369202 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[SH:12][CH2:13][CH:14]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C@H:18]([C:31]([OH:33])=[O:32])[CH2:19][C:20]1[CH:25]=[CH:24][C:23](C2SC=CC=2)=[CH:22][CH:21]=1)=[O:16].C(=O)(O)[O-].[K+]>C1(C)C=CC=CC=1>[SH:12][CH2:13][CH:14]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C@H:18]([C:31]([OH:33])=[O:32])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:22][CH:21]=1)=[O:16]

Participants

5

Reactant 3

HCID 201262(4-Methoxyphenyl)boronic acid2×HCID 516893Potassium BicarbonateHCID 54348658HCID 54348658, compound

Product 1

HCID 53688502HCID 53688502, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The operation is carried out as in Stage 1 of Example 10 using 4-methoxy benzeneboronic acid instead of thiophene-2-boronic acid, starting with 351.6 mg of 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, 250 mg of 4-methoxybenzene boronic acid, 170.3 mg of potassium bicarbonate and 190.17 mg of 5-tetrakis (triphenyl phosphine) Pd(O). In this way 199 mg of expected product is obtained.

Sources & evidence

ORD record
ord-40a9364876ad49b0b968a13b85bdab03
Source dataset
uspto-grants-2000_10
Patent number
US06136842

Reaction notes

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