Hydrochloric Acid → HCID 67022504, compound

HRID 1915967Notes

Reaction equation

HRID 1915967 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)[CH3:2].[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25]([NH:27][C:28]3([C:32](O)=[O:33])[CH2:31][CH2:30][CH2:29]3)=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1.[C:35]([O:39]C(NC1(C(O)=O)CC1)=O)(C)(C)C.C1CN([P+]([O:65]N2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC(OC)=O.C(C1CC1(N)C(O)=O)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>C(Cl)Cl.CC#N>[CH3:35][O:39][C:2](=[O:65])[CH2:1][NH:4][C:32]([C:28]1([NH:27][C:25]([O:24][CH2:23][CH:21]2[C:22]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]3[C:20]2=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:26])[CH2:31][CH2:30][CH2:29]1)=[O:33]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 69221Glycine methyl esterHCID 81531DiisopropylethylamineHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 15126471-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)cyclobutane-1-carboxylic acidHCID 2724699PyBOPHCID 56923991HCID 56923991, compound

Product 1

HCID 67022504HCID 67022504, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (2.60 mL, 14.82 mmol) was added to 1-(9H-Fluoren-9-ylmethoxy carbonylamino)-cyclobutanecarboxylic acid, 1 (2.0 g, 5.93 mmol) and PyBOP (3.393 g, 6.52 mmol) in CH2Cl2 (150 mL) at rt under Ar(g). After 10 minutes, MeCN (150 mL) and HCl.GlyOMe, 2 (819 mg, 6.52 mmol) were added. After 16 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography eluting with hexane/EtOAc (2:1 to 1:3) to yield 3 as a white solid (2.373 g, 98%).

Workup

  1. waitAfter 16 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography
  4. washeluting with hexane/EtOAc (2:1 to 1:3)

Sources & evidence

ORD record
ord-cd5d1b93f62548249152012bd0dc3044
Source dataset
uspto-grants-2013_12
Patent number
US08614193B2

Reaction notes

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