Benzyl Alcohol → Benzyl N-{1-Methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}carbamate

HRID 238940Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])C(O)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].CC[N:20]([CH2:23]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1(C)C=CC=CC=1>[CH3:17][C:12]([NH:20][C:23](=[O:32])[O:49][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=1)[CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 2-[4-(methylsulfonylamino)phenyl]-2-methylpropionic acid (8-11, 1 mmol) in toluene (6 mL) was treated with 4A molecular sieve (200 mg), Et3N (1.3 mmol) and diphenylphosphoryl azide (1.3 mmol) and heated at 110° C. for 1 h. The mixture was cooled to room temperature and BnOH (20 mmol) was added. After the mixture was heated to 110° C. for 12 hours and concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc:hexanes as eluant to afford Benzyl N-{1-Methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}carbamate (21-1, CHK-582)

Workup

temperatureThe mixture was cooled to room temperature
temperatureAfter the mixture was heated to 110° C. for 12 hours
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel with EtOAc

Sources & evidence

ORD record: ord-3431c1977d7a49658875a565c8b774b7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642657B2

Reaction notes

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