Dimethyl Sulfoxide → (2S,4S)-N-allyloxycarbonyl-2-[(E)-2-[4-(allyloxycarbonyl)piperazinylcarbonyl]vinyl]-4-tritylthiopyrrolidine

HRID 2371829Notes

Reaction equation

HRID 2371829 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32]O)=[O:6])[CH:2]=[CH2:3].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH2:51]([O:54][C:55]([N:57]1[CH2:62][CH2:61][N:60]([C:63](=[O:73])[CH2:64]P(OCC)(OCC)=O)[CH2:59][CH2:58]1)=[O:56])[CH:52]=[CH2:53].[H-].[Na+]>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1/[CH:32]=[CH:64]/[C:63]([N:60]1[CH2:59][CH2:58][N:57]([C:55]([O:54][CH2:51][CH:52]=[CH2:53])=[O:56])[CH2:62][CH2:61]1)=[O:73])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 6

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 10551897(2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-tritylthiopyrrolidineHCID 53984636N-allyloxycarbonyl-N'-(diethylphosphonoacetyl)piperazine

Product 1

HCID 67917267(2S,4S)-N-allyloxycarbonyl-2-[(E)-2-[4-(allyloxycarbonyl)piperazinylcarbonyl]vinyl]-4-tritylthiopyrrolidineYield 92.6%

Procedure

The same operation as in Reference Example 4-1) was carried out by using (2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-tritylthiopyrrolidine (the compound obtained in Reference Example 3-1); 1.5 g, 3.26 mmol), dimethyl sulfoxide (0.65 ml, 9.14 mmol), oxalyl chloride (0.42 ml, 4.90 mmol), triethylamine (2 ml, 14.9 mmol), N-allyloxycarbonyl-N'-(diethylphosphonoacetyl)piperazine (1.24 g, 3.92 mmol) and 60% sodium hydride (130 mg, 3.26 mmol), followed by flash column chromatographic purification on silica gel (Wakogel® C-300, 40 ml, elution with ethyl acetate) to give the title compound (1.97 g, 92.6% yield).

Workup

  1. customobtained in Reference Example 3-1)

Sources & evidence

ORD record
ord-7f79c76b3a1e497797197805c1204bef
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

Loading…