Methanesulfonyl chloride → HCID 86584381, compound

HRID 393800Notes

Reaction equation

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

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 12115013(3R,4R)-3-(Boc-amino)-1-Cbz-4-(hydroxymethyl)pyrrolidine

Product 1

HCID 86584381HCID 86584381, compoundYield 99%

Procedure

The product of Example 54B (4.2 g, 12 mmol) was treated with methanesulfonyl chloride according to the procedure described in Example 38G. The title compound was obtained as a brown oil (5.10, 99% yield). 1H NMR (MeOH-D4, 300 MHz) δ1.46 (s, 9H), 2.80 (m, 1H), 3.08 (s, 3H), 3.40 (m, 2H), 3.70 (m, 2H), 4.16 (m, 1H), 4.35 (m, 2H), 5.16 (s, 2H), 7.30 (m, 5H); MS (DCI/NH3) m/z 446 (M+NH4)+, 429 (M+H)+.

Sources & evidence

ORD record: ord-ece8365b53484e56b60478043ed54245
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809105B2

Reaction notes

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