Triethylazanium;formate → H2N-(CH2)2-N(Boc)-(CH2)2-CONH-(CH2)2-STrt

HRID 1399501Notes

Reaction equation

HRID 1399501 reaction equation
C([NH:7][CH2:8][CH2:9][N:10]([CH2:18][CH2:19][C:20]([NH:22][CH2:23][CH2:24][S:25][C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:21])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(OCC=C)=O.C([O-])=O.C([NH+](CC)CC)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][CH2:8][CH2:9][N:10]([CH2:18][CH2:19][C:20]([NH:22][CH2:23][CH2:24][S:25][C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:21])[C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 10219518Triethylazanium;formateHCID 131732134Alloc-NH-(CH2)2-N(Boc)-(CH2)2-CONH-(CH2)2-STrt

Product 1

HCID 70987991H2N-(CH2)2-N(Boc)-(CH2)2-CONH-(CH2)2-STrt

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Alloc-NH—(CH2)2—N(Boc)-(CH2)2—CONH—(CH2)2-STrt (48.3 mg, 0.078 mmol) was dissolved in THF, triethylammoniumformate (62 μl) and Pd(PPh3)4 (16 mg) were added. The solution was stirred for 12 h at RT and monitored by MS. After completion the solvent was removed in vacuo. The residue was dissolved in MeCN/H2O (50:50, with 0.1% TFA) and purified by RP-HPLC to give H2N—(CH2)2—N(Boc)-(CH2)2—CONH—(CH2)2-STrt (31).

Workup

  1. customAfter completion the solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in MeCN/H2O (50:50, with 0.1% TFA)
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-8da5eb13bb2648c996d4ada83fa5161e
Source dataset
uspto-grants-2014_12
Patent number
US08906847B2

Reaction notes

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