Benzoic Acid → HCID 24798586, compound

HRID 492081Notes

Reaction equation

HRID 492081 reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].Cl[Si](C)(C)C.CCN([CH:18]([CH3:20])[CH3:19])C(C)C.Cl[C:22]([O:24][CH:25](Cl)[CH:26]([CH3:28])[CH3:27])=[O:23].[C:30]([OH:38])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl>[CH3:2][N:1]([C:22]([O:24][CH:25]([C:26]1[CH:28]=[CH:19][CH:18]=[CH:20][CH:27]=1)[O:38][C:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:37])=[O:23])[CH2:3][C:4]([OH:6])=[O:5]

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 1088SarcosineHCID 6397ChlorotrimethylsilaneHCID 81531Diisopropylethylamine2×HCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 24798586HCID 24798586, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the general procedure for the one pot synthesis, sarcosine (1.0 g, 11.2 mmol) was reacted with chlorotrimethylsilane (2.8 mL, 22.4 mmol) in anhydrous chloroform (25 mL) in the presence of DIEA (4.1 mL, 22.4 mmol). Subsequent reaction of the intermediate with 1-chloro-2-methylpropyl chloroformate (4.59 g, 22.4 mmol) followed by a mixture of DIEA (4.1 mL, 22.4 mmol) and benzoic acid (2.8 g, 22.4 mmol) provided 0.622 g (16.3% yield) of the title compound (50) as a buff-colored solid after aqueous work-up and mass-guided preparative HPLC purification. 1H NMR (CD3OD, 400 MHz): δ=8.13 (d, 2H), 7.81 (d, 1H), 7.61 (m, 3H), 7.57 (m, 5H), 4.10 (br m, 2H), 3.01 (2s, 3H). MS (ESI) m/z 366.14 (M+Na)+.

Sources & evidence

ORD record
ord-22348e3883e14a1fb88d8482a0f420a2
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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