4-Nitrophenyl chloroformate → HCID 58557070, compound

HRID 1969929Notes

Reaction equation

HRID 1969929 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([OH:30])[CH2:4]1)[CH3:2].[C:31](Cl)(=[O:42])[O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)O[C@@H]1C[C@H](C2N3C4C=CN(S(C5C=CC(C)=CC=5)(=O)=O)C=4N=CC3=NN=2)[C@H](CC)C1>[C:31](=[O:42])([O:32][C:33]1[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=1)[O:30][CH:5]1[CH2:6][CH:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH:3]([CH2:1][CH3:2])[CH2:4]1

Participants

6

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 67999683HCID 67999683, compound

Product 1

HCID 58557070HCID 58557070, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 58558041HCID 58558041, compoundSolvent

Procedure

To a scalemic mixture enriched in (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol (6.11 g, 14.4 mmol) in pyridine (100 mL) was added DMAP (1.93 g, 15.8 mmol) and 4-nitrophenyl carbonochloridate (4.34 g, 21.5 mmol). The resulting mixture was stirred at ambient temperature for about 3.5 h and heated at about 33° C. for about 1 h. The solid was filtered off and washed with EtOAc (30 mL). The filtrated was concd under reduced pressure. The residue was purified using silica gel chromatography eluting with 0-30% EtOAc in heptane to give a scalemic mixture enriched in (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl 4-nitrophenyl carbonate (6.63, 78%). LC/MS (Table 1, Method b) Rt=2.65 min; MS m/z: 591 (M+H)+.

Workup

  1. temperatureheated at about 33° C. for about 1 h
  2. filtrationThe solid was filtered off
  3. washwashed with EtOAc (30 mL)
  4. customThe residue was purified
  5. washeluting with 0-30% EtOAc in heptane
  6. customto give a scalemic mixture

Sources & evidence

ORD record
ord-59d19912a91749b3b5e66804de6aec8e
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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