Formic Acid → HCID 145857223, compound

HRID 11008Notes

Reaction equation

HRID 11008 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH:16](O)=[O:17].[CH2:19]([O:26][C:27](=[O:67])[N:28]([CH2:64][CH:65]=[CH2:66])[C:29]1[C:34](=[O:35])[N:33]2[C@H:36]([C:41](=[O:63])[NH:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([C:50]([NH:52][C:53]([O:55][CH2:56][C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)=[O:54])=[NH:51])=[CH:46][CH:45]=3)[CH2:37][C@:38]([NH2:40])([CH3:39])[C:32]2=[N:31][CH:30]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:19]([O:26][C:27](=[O:67])[N:28]([CH2:64][CH:65]=[CH2:66])[C:29]1[C:34](=[O:35])[N:33]2[C@@H:36]([C:41](=[O:63])[NH:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([C:50]([NH:52][C:53]([O:55][CH2:56][C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)=[O:54])=[NH:51])=[CH:46][CH:45]=3)[CH2:37][C@@:38]([NH:40][CH:16]=[O:17])([CH3:39])[C:32]2=[N:31][CH:30]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 145857227benzyl N-[(6S,8R)-8-amino-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

Product 1

HCID 145857223HCID 145857223, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of DCC (18.6 mg, 0.090 mmol) and formic acid (8.28 mg, 0.180 mmol) in CH2Cl2 that had been stirred at 0° C. for 10 min, was added intermediate 26a (30 mg, 0.045) in a solution of pyridine. The reaction was stirred at 0° C. for 15m then at rt for 2 h. The reaction mixture was concentrated in vacuo, then taken up in brine and extracted with chloroform (6×), dried (Na2SO4) and concentrated. It was purified by SiO2 chromatography (gradient elution, 1–12% MeOH/CH2Cl2) to afford 23.3 mg (75%) of intermediate 42a. MS (ESI) 692.2 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with chloroform (6×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customIt was purified by SiO2 chromatography (gradient elution, 1–12% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8aca7148692f4ee8a269e8efde4e1fcd
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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