Diisopropylethylamine → HCID 86659035, compound

HRID 1429317Notes

Reaction equation

HRID 1429317 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:12]([CH:15]([CH2:19][C:20]#[CH:21])[C:16](O)=O)[C:13]#[CH:14].CN([C:25]([O:29]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CC#N>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:10][NH:11][C:25](=[O:29])[CH2:16][CH:15]([CH2:19][C:20]#[CH:21])[CH2:12][C:13]#[CH:14])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136736532-(prop-2-yn-1-yl)pent-4-ynoic acid

Product 1

HCID 86659035HCID 86659035, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N-boc-ethylenediamine (18.3 gm, 0.1143 mol) in 50 ml of CH3CN was added slowly via an addition funnel to a stirred solution containing dipropargylacetic acid (15.56 gm, 0.1143 mol), TBTU (36.74 gm, 0.114 mol) and DIPEA (29.6 gm, 0.229 mol) in 300 ml of CH3CN at 0 C. Precipitation occurred. The ice bath was removed and the product was stirred at ambient temperature overnight (16 hours). The reaction was now totally homogeneous. The solution was concentrated in vacuo and the residue was diluted with 800 ml of water. The resulting solids were filtered, washed copiously with water, and vacuum dried to give 14.3 gm of crude product. Re-crystallization (2×) from DCM, filtration and washing with hexanes affords the product (9.85 gm, 31% yield, 98% purity by HPLC (214 nm)).

Workup

  1. customPrecipitation
  2. customThe ice bath was removed
  3. concentrationThe solution was concentrated in vacuo
  4. additionthe residue was diluted with 800 ml of water
  5. filtrationThe resulting solids were filtered
  6. washwashed copiously with water, and vacuum
  7. customdried

Sources & evidence

ORD record
ord-7e508cfe716944e7b2f0032ce1367bf3
Source dataset
uspto-grants-2015_01
Patent number
US08940690B2

Reaction notes

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