Chloroacetyl chloride → HCID 21072072, compound

HRID 729205Notes

Reaction equation

HRID 729205 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-b680c03504104b91a6c1bebf1ef51542
Source dataset
uspto-grants-2009_09
Patent number
US07582280B2

Reaction notes

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