Triethylamine → HCID 86747291, compound

HRID 1656156Notes

Reaction equation

HRID 1656156 reaction equation
FC(F)(F)C(O)=O.[I:8][CH:9]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])[C:10]#[CH:11].C(N(CC)CC)C.[C:25]([O:29][C:30]([NH:32][CH2:33][C:34](O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[I:8][CH:9]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH:15][C:34](=[O:35])[CH2:33][NH:32][C:30]([O:29][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:31])[C:10]#[CH:11]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86747292HCID 86747292, compound2×

Product 1

HCID 86747291HCID 86747291, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred, anhydrous dichloromethane (30 ml.) solution of L-alanine iodopropargyl ester trifluoroacetate (Compound #8) (2.30 g., 6.27 mmole) held at 0° C. with an ice-bath was added triethylamine (0.96 ml., 6.89 mmole), followed by N-t-butoxycarbonylglycine (1.10 g., 6.28 mmole), 1-hydroxybenzotriazole hydrate (0.85 g., 6.29 mmole) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.56 g., 8.14 mmole). The reaction mixture was held at 0°-7° C. for 17 hours. The resultant solution was transferred to a separatory funnel and diluted to an approximate volume of 100 ml. with dichloromethane, then washed successively with 3×50 ml. of water, 3×50 ml. of 10% aqueous potassium hydrogen sulfate, 3×50 ml. of saturated aqueous sodium bicarbonate, 3×50 ml. of water and a final wash with 50 ml. of saturated aqueous sodium chloride. The organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo with a rotary evaporator to give 1.80 g. (70% yield) of the desired N-t-butoxycarbonylglycyl-L-alanine iodopropargyl ester as a dry white foam. 1H-NMR (200 MHz, CDCl3) δ=1.45 ppm, d, 3H; 1.45, 1.72, two s, 9H; 3.82, d, 2H; 4.63, m, 1H; 4.87, s, 2H; 5.17, broad m, 1H; 6.67, d, 1H.

Workup

  1. additiondiluted to an approximate volume of 100 ml
  2. washwith dichloromethane, then washed successively with 3×50 ml
  3. washof water and a final wash with 50 ml
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo with a rotary evaporator
  7. customto give 1.80 g

Sources & evidence

ORD record
ord-c4c9746ae5704381b3ac975993c8590c
Source dataset
uspto-grants-1993_10
Patent number
US05252745

Reaction notes

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