Hydrochloric Acid → HCID 58017467, compound

HRID 1879230Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:27])[C@@H:10]([C:23]([CH3:26])([CH3:25])[CH3:24])[NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38].Cl>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:27])[C@@H:10]([C:23]([CH3:24])([CH3:26])[CH3:25])[N:11]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)(=[O:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-(3 Methoxyphenylsulfonyl)D-tert-leucine benzyl ester (1.31 g, 3.35 mmol) in DMF (10 ml) is added K2CO3 (1.87 g, 13.4 mmol) followed by 1-iodo-3-methyl butane (1.33 g, 6.69 mmol) and the reaction mixture is heated to 70° C. overnight. The reaction is cooled to room temperature and then poured over 1 N HCl and extracted with Ethyl Acetate. The organics are washed with brine, dried over MgSO4 and concentrated. The crude product is purified by column chromatography eluting with a gradient of 5-40% (Hex-EtOAc) affording the title compound as a colorless oil (1.0 g, 65% yield). Mass spectrum (462.3; M+1).

Workup

temperatureThe reaction is cooled to room temperature
extractionextracted with Ethyl Acetate
washThe organics are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product is purified by column chromatography
washeluting with a gradient of 5-40% (Hex-EtOAc)

Sources & evidence

ORD record: ord-6abd9df5b8964b86a4fda629429fe7f6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314148B2

Reaction notes

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