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Dichloromethane → Chloromethyl 2-{[(tert-butoxy)carbonyl]amino}acetate

HRID 1056577
Notes
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Reaction equation

HRID 1056577 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[CH2:18](Cl)[Cl:19]>O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][CH2:18][Cl:19])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium Bicarbonate

Product 1

HCID 12968718Chloromethyl 2-{[(tert-butoxy)carbonyl]amino}acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to the procedure as described in Example 17 Step 1 using 2-((tert-butoxycarbonyl)amino)acetic acid (1 g, 5.7 mmol) in DCM (25 mL) and H2O (25 mL), NaHCO3 (1.92 g, 22.8 mmol), TBAHSO4 (194 mg, 0.57 mmol) and a solution of chloromethyl sulfochloridate (693 mL, 6.8 mmol) in DCM (5 mL). The title compound was obtained as colorless oil (911 mg, 71.3%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0088c5696bdd4a198c42c89ac1a3e887
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09399639B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes