Water → HCID 59710633, compound

HRID 2221124Notes

Reaction equation

[F-:1].[K+].[C:3]([S:22][CH2:23][CH2:24][NH:25][C:26]([C:28]1[CH:39]=[CH:38][C:31]([CH2:32]OS(C)(=O)=O)=[CH:30][CH:29]=1)=[O:27])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>C(#N)C>[F:1][CH2:32][C:31]1[CH:38]=[CH:39][C:28]([C:26]([NH:25][CH2:24][CH2:23][S:22][C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:27])=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of Kryptofix (Fluka, 15 mg, 40 μmol) in dry acetonitrile (200 μl) was added to solid potassium fluoride (2.3 mg, 80 μmol). The mixture was shaken for 5 min. The Kryptofix/KF-solution was added to a solution of methanesulphonic acid 4-[2-(tritylsulphanyl)ethylcarbamoyl]benzyl ester (21 mg, 40 μmol) in acetonitrile (400 μl). The mixture was heated at 65° C. for 10 min. An aliquot was analysed by HPLC (column Phenomenex Luna 3 μm C18(2) 50×4.60 mm; solvents: A=water/0.1% TFA and B=acetonitrile/0.1% TWA; gradient 40-80% B over 10 min; flow 2.0 ml/min, UV detection at 214 and 254 nm), showing complete conversion of starting material (tR 5.6 min) to a new product (tR 6.3 min). Purification by reverse phase preparative HPLC (column: Phenomenex Luna C18(2) 5 μm 250×21.2 mm, solvents: A=water/0.1% TFA and B=acetonitrile/0.1% TFA; gradient 40-80% B over 60 min; flow 10.0 ml/min, UV detection at 214 nm) gave 4.5 mg of white solid. The structure was confirmed by NMR spectroscopy.

Workup

waitgradient 40-80% B over 10 min
customPurification by reverse phase preparative HPLC (column
waitgradient 40-80% B over 60 min

Sources & evidence

ORD record: ord-6f5787ae99dd44219b2546ae3b546573
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368474B2

Reaction notes

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