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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 269648Generated: October 25, 2026

1,2-Dichloroethane → Benzyl [(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate

https://huagongshe.com/reaction/269648

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantN-((Phenylmethoxy)carbonyl)-O-(phenylmethyl)-L-serineHCID 6993425—
Reactanttert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamateHCID 57440197—
SolventDimethylformamideHCID 6228—
ProductBenzyl [(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamateHCID 86624498—

Reaction Steps

Preparation takes place in analogy to Example 79A from 150 mg (0.46 mmol) of O-benzyl-N-[(benzyloxy)carbonyl]-L-serine and 188 mg (0.59 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) in 6 ml of dimethylformamide with the addition of 114 mg (0.57 mmol) of EDC and 18 mg (0.13 mmol) of HOBt. The product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→5:95).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07446102B2
Source datasetuspto-grants-2008_11
ORD IDord-fde0cb4cf4fd40a09c776538310135cc
Source noteuspto-grants-2008_11