HCID 71114306, compound → HCID 58571238, compound

HRID 511041Notes

Reaction equation

HRID 511041 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.C(NCC)C>[NH2:1][C@H:2]([C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 71114306HCID 71114306, compound

Product 1

HCID 58571238HCID 58571238, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

To a solution of Fmoc-Asn(Trt)-OBn (3.5 g, 5.1 mmol) in DCM (14.0 mL), diethylamine (14.0 mL) was added and stirred for 1 h at rt. The resulting solution was concentrated in vacuo and the thick-residue was purified by neutral alumina column chromatography (eluent: 0-50% EtOAc in Hexane then 0-5% MeOH in CHCl3) to yield NH2-Asn(Trt)-OBn D (yield: 1.75 g, 73.0%; Mass: Cal. 464.21, Obs—465.3 (M+1), 487.2 (M+Na]).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customthe thick-residue was purified by neutral alumina column chromatography (eluent

Sources & evidence

ORD record
ord-2341bab2d82649c18cd4f599a03bba82
Source dataset
uspto-grants-2015_08
Patent number
US09096642B2

Reaction notes

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