Triethylamine → HCID 86646817, compound

HRID 1697549Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[N+:18]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].CCN(CC)CC.C(OC(C)(C)C)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:4]1[CH2:8][C@H:7]([O:9][S:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)(=[O:28])=[O:29])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:17]

Participants

Conditions

Temperature: 2.5 °C

Procedure

N-Boc-cis-4-hydroxy proline methyl ester (1.0 eq, 6.0 g) were dissolved in MeCl2 (60.0 ml) and 3-nitrobenzenesulfonyl chloride (1.06 eq; 5.747 g) was added. This clear colorless solution was cooled to 0-5° C. and the Et3N (3.0 eq., 10.19 ml) was carefully added. After 0.5 h a yellowish thin suspension was formed, which was stirred for 18 h at ambient temperature. The mixture turned then into a light brown suspension. LC-MS-analysis revealed that the reaction was complete. The reaction mixture was diluted with additional MeCl2 (100 ml) and extracted in succession with aq. 0.5 N HCl, 10% Na2CO3. The combined org. layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to yield a light brown viscous oil (10.8 g; 102%). MS (ESI): m/z=331.2 [M+H-Boc]+

Workup

customAfter 0.5 h a yellowish thin suspension was formed
extractionextracted in succession with aq. 0.5 N HCl, 10% Na2CO3
washlayers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated to dryness
customto yield a light brown viscous oil (10.8 g; 102%)

Sources & evidence

ORD record: ord-012b0c8cebec4d0bb8942d000c9f86dc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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