Sodium → HCID 57285623, compound

HRID 1492810Notes

Reaction equation

C([N:8]1[CH:11]([C@@H:12]2[CH2:16][C@@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][N:13]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:10][C:9]1=[O:32])C1C=CC=CC=1.[Na]>>[NH:8]1[CH:11]([C@@H:12]2[CH2:16][C@@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][N:13]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:10][C:9]1=[O:32]

Participants

Reactant 2

HCID 5360545Sodium

HCID 57319918HCID 57319918, compound

Product 1

HCID 57285623HCID 57285623, compoundYield 88.4%

Procedure

The same procedure as in Reference Example 3-3 was carried out by using (2S,4R)-2-(N-benzyl-2-azetidinon-4-yl)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxypyrrolidine diastereomer A (500 mg, 1.05 mmol) and sodium metal (75 mg, 3.26 mmol) to obtain (2S,4R)-2-(2-azetidinon-4-yl)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxypyrrolidine diastereomer A (360 mg, yield: 88.4%).

Sources & evidence

ORD record: ord-1936c808184c48cb983160334dfc07e4
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374720

Reaction notes

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