Acetic Acid → 2-[2-oxo4-(1H-tetrazol-1-yl)-1-pyrrolidinyl]butanamide

Reaction equation

[NH2:1][CH:2]1[CH2:6][N:5]([CH:7]([CH2:11][CH3:12])[C:8]([NH2:10])=[O:9])[C:4](=[O:13])[CH2:3]1.[N-:14]=[N+:15]=[N-:16].[Na+].[CH3:18]C(O)=O>>[O:13]=[C:4]1[CH2:3][CH:2]([N:1]2[CH:18]=[N:16][N:15]=[N:14]2)[CH2:6][N:5]1[CH:7]([CH2:11][CH3:12])[C:8]([NH2:10])=[O:9]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 33557Sodium Azide

HCID 22386994HCID 22386994, compound

Product 1

HCID 223870622-[2-oxo4-(1H-tetrazol-1-yl)-1-pyrrolidinyl]butanamide

Procedure

Alternatively to § 5.6, reaction of 2-[4-amino-2-oxo-1-pyrrolidinyl]butanamide with triethyl orthoformiate, NaN3 and AcOH provided 2-[2-oxo-4-(1H-tetrazol-1-yl)-1-pyrrolidinyl]butanamide 67.

Sources & evidence

ORD record: ord-c42955d687ae4ec8993107fedb51820f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692028B2

Reaction notes

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