Glycine methyl ester → HCID 178501653, compound

HRID 574677Notes

Reaction equation

HRID 574677 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]([NH:10][C:11]2[C:12]([OH:20])=[N:13][C:14]([C:17](O)=[O:18])=[N:15][CH:16]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CS(C)=O>[C:1]1([CH:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:8]([NH:10][C:11]2[C:12]([OH:20])=[N:13][C:14]([C:17]([NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:18])=[N:15][CH:16]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 69221Glycine methyl esterHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178524896HCID 178524896, compound

Product 1

HCID 178501653HCID 178501653, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Step A product, 3-1-a, (300 mg, 0.86 mmol), methyl 2-aminoacetate (129 mg, 1.03 mmol) and DIEA (222 mg, 1.7 mmol) in DMSO (10 mL) was added with TBTU (330 mg, 1.03 mmol) and stirred at room temperature for overnight. The reaction mixture was poured into ice water (100 mL). The solids were filtered and purified by pre-HPLC to afford the product as a white solid, 3-1-b, (60 mg, 17%). LC-MS (M+H)+ 421.0

Workup

  1. filtrationThe solids were filtered
  2. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-0f21a5ae20814a7f983f3b4dca221942
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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