Chloroacetyl chloride → HCID 21072072, compound

HRID 2217099Notes

Reaction equation

HRID 2217099 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:13])[CH2:11][NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:14][CH2:15][C:16](Cl)=[O:17].C([O-])([O-])=O.[K+].[K+]>>[CH2:2]([O:9][C:10](=[O:13])[CH2:11][NH:12][C:16](=[O:17])[CH2:15][Cl:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 11701227Benzyl 2-aminoacetate hydrochloride2×

Product 1

HCID 21072072HCID 21072072, compound

Procedure

DOTA-G-tri-t-butyl ester 4, an intermediate compound in the synthesis of the conjugate 22, was synthesized starting with glycine benzylester hydrochloride (Aldrich), as described in Scheme 1. Chloroacetylchloride (Aldrich) was added to glycine benzylester hydrochloride in the presence of K2CO3 to produce N-(chloroacetyl)-glycine benzyl ester 1. The ester 1 was added to a suspension of DO3A-tri-t-butyl ester hydrochloride 2 (see U.S. Pat. No. 5,573,752) in K2CO3 to produce DOTA-G-tri-t-butyl-benzyl ester 3. Subsequent catalytic hydrogenation produced the DOTA-G-tri-t-butyl ester 4.

Workup

  1. customwas synthesized

Sources & evidence

ORD record
ord-6ac5e631c7ad4b79bb21642bcc6237f1
Source dataset
uspto-grants-2008_08
Patent number
US07407644B2

Reaction notes

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