Triethylamine → HCID 57046554, compound

HRID 1492819Notes

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][CH:33]1[CH2:37][N:36]([C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[C@H:35]([C:44]([OH:46])=O)[CH2:34]1)=[O:6])[CH:2]=[CH2:3].ClC(OCC(C)C)=O.[CH2:55]([N:57](CC)[CH2:58]C)C>>[CH3:5][NH:7][CH3:8].[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:9][C@H:8]1[CH2:32][CH:33]1[CH2:37][N:36]([C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[C@H:35]([C:44](=[O:46])[N:57]([CH3:58])[CH3:55])[CH2:34]1)=[O:6])[CH:2]=[CH2:3]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 62365Isobutyl chloroformate

HCID 57323092HCID 57323092, compound

Product 2

HCID 674DimethylamineYield 50%

HCID 57046554HCID 57046554, compoundYield 184.8%

Procedure

The same procedure as in Reference Example 25-8 was carried out by using (2R,4S)-N-allyloxycarbonyl-2-[(2S)-N-allyloxycarbonyl-2-carboxypyrrolidin-4-ylmethyl]-4-tritylthiopyrrolidine (300 mg, 0.47 mmol), isobutyl chloroformate (74 μl, 0.56 mmol), triethylamine (78 μl, 0.56 mmol) and a 50% dimethylamine aqueous solution (0.27 ml) to obtain (2R,4S)-N-allyloxycarbonyl-2-[(2S)-N-allyloxycarbonyl- 2-(dimethylcarbamoyl)pyrrolidin-4-ylmethyl]-4-tritylthiopyrrolidine (290 mg, yield: 93%).

Sources & evidence

ORD record: ord-2514b175a29245b485e33204009c2b75
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374720

Reaction notes

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