Triethylamine → HCID 86589077, compound

HRID 2084982Notes

Reaction equation

HRID 2084982 reaction equation
C1(C([O:14][C:15](=[O:53])[C@H:16]2[CH2:20][C@@H:19]([N:21]3[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[N:24]([C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:22]3=[O:23])[CH2:18][N:17]2CCNS(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)C2C=CC=CC=2)C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:30]([N:24]1[C:25](=[O:26])[C:27]([CH3:28])=[CH:29][N:21]([C@H:19]2[CH2:18][NH:17][C@@H:16]([C:15]([OH:53])=[O:14])[CH2:20]2)[C:22]1=[O:23])(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 21305426HCID 21305426, compound

Product 1

HCID 86589077HCID 86589077, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-Nitrobenzenesulfonamidoethyl)-cis-4-(benzoylthymin-1-yl)-D-proline diphenylmethyl ester (5) (1.20 g, 0.46 mmol) was dissolved in dichloromethane (5 mL). Boc2O (110 mg, 0.50 mmol) and triethylamine (5 mL) was added with stirring followed by 4-dimethylaminopyridine (10 mg, cat.). The yellow solution was stirred at room temperature for 6.5 h then evaporated to dryness to give N-2-(N′-4-Nitrobenzenesulfonyl-N′-tert-butoxycarbonyl)aminoethyl)-cis-4-(benzoylthymin-1-yl)-D-proline as yellow foam. Treatment of this material (max 0.46 mmol) with anhydrous K2CO3 (85 mg, 0.60 mmol) and thiophenol (66 mg, 0.60 mmol) in DMF (2 mL) at room temperature afforded an orange-yellow solution. The reaction mixture was then diluted with dichloromethane, washed with water and evaporated to dryness. The resulting yellow oil was purified by column chromatography (SiO2; EtOAc:Light Petroleum 1:1→2:1) to give the product as white foam 186.3 mg (62%, 2 steps); δH (200 MHz; CDCl3) 1.46 [9H, s, tBu CH3], 1.90 [3H, s, thymine CH3], 1.95 and 2.60 [2H, 2×m, CH2(3′)], 2.70-3.30 [6H, m, CH2(5′) and 2×aminoethyl CH2], 3.42 [1H, dd, CH(2′)], 5.12 [1H, m, CH(4′)], 5.28 [1H, br m, NH], 6.98 [1H, s, CHPh2], 7.36 [10H, m, Dpm aromatic CH], 7.50 [2H, t, Bz m-CH], 7.63 [1H, t, Bz p-CH], 7.90 [2H, d, Bz o-CH] and 7.98 [1H, s, thymine C(6)H]; m/z (APCI+) 676 (M+Na+, 18.5%), 653 (M+H+, 59), 597 (M−C4H8+, 25), 554 (M−Boc+, 9), 475 (26.5), 167 (Ph2CH+, 100); [α]D22+6.5 (c=1.06, CHCl3)

Workup

  1. stirringThe yellow solution was stirred at room temperature for 6.5 h
  2. customthen evaporated to dryness

Sources & evidence

ORD record
ord-3432482a437145eb922ba3d6b4409508
Source dataset
uspto-grants-2004_04
Patent number
US06716961B2

Reaction notes

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