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Tert-butyl N-[(3S)-2-oxoazetidin-3-yl]carbamate → HCID 131714546, compound

HRID 482924
Notes
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Reaction equation

HRID 482924 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][NH:11][C:10]1=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[N:19]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:20]=[S:21]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][N:11]([C:20](=[S:21])[NH:19][CH2:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C:10]1=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11116749Tert-butyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 20243554Tert-butyl 2-isothiocyanatoacetateHCID 178418339Butyllithium

Product 1

HCID 131714546HCID 131714546, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

A solution of (S)-3-[[(t-butyloxy)carbonyl]amino]-2-azetidinone (186 mg, 1 mmol) in 6 ml of dry tetrahydrofuran at -75° C. was treated with 0.65 ml (1.1 mmol) of 1.68N n-butyl lithium. After 30 minutes, a solution of t-butyl isothiocyanatoacetate (0.17 ml, 1.1 mmol) in 1 ml of dry tetrahydrofuran was added to the reaction mixture. After stirring at -75° C. for 2 hours, the reaction mixture was placed at -70° C. overnight.

Workup

  1. waitthe reaction mixture was placed at -70° C. overnight

Sources & evidence

ORD record
ord-30af46f0d4664fd1890db0e5a37d6115
Source dataset
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04576749

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes