1,4-Dihydro-2,4-dioxo-2H-3,1-benzoxazine-6-sulfonyl chloride → (2S,4R)-6-(2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl)-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1006826Notes

Reaction equation

HRID 1006826 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:35]=[C:36]1[NH:41][C:40]2[CH:42]=[CH:43][C:44]([S:46](Cl)(=[O:48])=[O:47])=[CH:45][C:39]=2[C:38](=[O:50])[O:37]1>>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:12][N:11]1[S:46]([C:44]1[CH:43]=[CH:42][C:40]2[NH:41][C:36](=[O:35])[O:37][C:38](=[O:50])[C:39]=2[CH:45]=1)(=[O:47])=[O:48])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 226716181,4-Dihydro-2,4-dioxo-2H-3,1-benzoxazine-6-sulfonyl chlorideHCID 69427603(2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine

Product 1

HCID 86584854(2S,4R)-6-(2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl)-1H-benzo[d][1,3]oxazine-2,4-dione

Procedure

In analogy: (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine and 2,4-dioxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-6-sulfonyl chloride [Ferrini et al. Eur. Pat. Appl. No. 800220] gave (2S,4R)-6-(2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl)-1H-benzo[d][1,3]oxazine-2,4-dione, MS: 689(M−H−), which was deprotected (following Method 3) to give (2S,4R)-6-(2-benzyloxymethyl-4-mercapto-pyrrolidine-1-sulfonyl)-1H-benzo[d][1,3]oxazine-2,4-dione, MS: 447 (M−H−).

Sources & evidence

ORD record
ord-695305dc8882403698afc1d3e58c5888
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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