Pyrrolidine → HCID 58043119, compound

HRID 1035225Notes

Reaction equation

HRID 1035225 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([O:10][C:11]([N:13]1[CH2:16][CH:15]([S:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[N:1]1([C:22]([C:21]2[CH:20]=[CH:19][C:18]([S:17][CH:15]3[CH2:16][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:14]3)=[CH:26][CH:25]=2)=[O:23])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58043139HCID 58043139, compound

Product 1

HCID 58043119HCID 58043119, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Pyrrolidine (0.60 g, 8.4 mmol) was added to a solution of 59B (2.0 g, 6.5 mmol) and DCM (25 mL). The mixture was cooled to 0° C. and then DIPEA and TBTU were added in the given order. The mixture was stirred at 0° C. for 20 min and then at RT for 1.5 h. The solution was washed with aqueous Na2CO3 (1M) and then the organic solution was evaporated. The product was purified by silica-gel chromatography using 1-5% methanol in DCM. There was obtained 2.3 g (98%) of 59C as an oil. 1H NMR (500 MHz, CDCl3): δ 1.42 (s, 9H), 1.89 (m, 4H), 3.41 (m, 2H), 3.62 (m, 2H), 3.86 (m, 2H), 4.04 (m, 1H), 4.34 (m, 2H), 7.19 (d, 2H), 7.45 (d, 2H), MS (APCI+) m/z 363 [M+H]+.

Workup

  1. waitat RT for 1.5 h
  2. washThe solution was washed with aqueous Na2CO3 (1M)
  3. customthe organic solution was evaporated
  4. customThe product was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-449a3675f0c94cb1bcb73303fe5a5b41
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…