Glycine → Fmoc-Gly-OH

HRID 1748847Notes

Reaction equation

HRID 1748847 reaction equation
[NH:1]([C:6]([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:2][C:3]([OH:5])=[O:4].N(C(OCC=C)=O)CC(O)=O.N1CCCCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NC(C1C(OC)=C(C=C([N+]([O-])=O)C=1)OCCCC(O)=O)C.NCC(O)=O>CN(C=O)C>[C:6]([NH:1][CH2:2][C:3]([OH:5])=[O:4])([O:8][CH2:9][CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7]

Participants

7

Reactant 5

HCID 750GlycineHCID 8082PiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68945927HCID 68945927, compoundHCID 131730075HCID 131730075, compound

Product 1

HCID 93124Fmoc-Gly-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

FmocGly/AllocGly beads were standard Fmoc deprotected with 20% piperidine in DMF leaving the Alloc glycine untouched. Then standard TBTU coupling of the Holmes photolinker (4-(1-aminoethyl-2-methoxy-5-nitrophenoxy)butanoic acid) to the deprotected glycine (1 eq=0.48 mmol). After coupling, the beads were washed with DMF and DCM and lyophilized.

Workup

  1. washthe beads were washed with DMF and DCM

Sources & evidence

ORD record
ord-f0342f9f64e64b339a0be7ef5c7c7049
Source dataset
uspto-grants-2015_10
Patent number
US09150899B2

Reaction notes

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