Ethyl Acetate → tert-butyl (aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]carbamate

HRID 222207Notes

Reaction equation

HRID 222207 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@H:10]1[CH2:33]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:35]([NH:42][SH:43](=[O:45])=[O:44])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.[N:71](C(OCC)=O)=NC(OCC)=O>>[C:38]([O:37][C:35](=[O:36])[N:42]([S:43]([NH2:71])(=[O:44])=[O:45])[CH2:33][C@@H:10]1[CH2:11][C@@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:13][C@@H:9]1[O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 5

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58944620((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanolHCID 178454374HCID 178454374, compound

Product 1

HCID 58944590tert-butyl (aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]carbamate

Conditions

Temperature
50 °C

Procedure

((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol (700.0 mg, 0.001462 mol), N-Boc-sulfonamide (398 mg, 0.00203 mol) and triphenylphosphine (575 mg, 0.00219 mol) were dissolved in ethyl acetate (28 mL, 0.28 mol) at 50° C. under an atmosphere of nitrogen. Diethyl azodicarboxylate (350.0 μL, 0.002223 mol) was added over 2-3 min and the mixture was stirred at 50° C. for 30 minutes. The cooled mixture was evaporated and the residue purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product as a white solid, 636 mg (66%). LC/MS: Rt=2.55 min, ES+ 657 (AA standard).

Workup

  1. customThe cooled mixture was evaporated
  2. customthe residue purified by silica gel chromatography
  3. washeluting with 10 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-36d443cc80da4bb0af19d05798217455
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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