1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl Boc-glycylglycyl-L-phenylalaninate

HRID 571440Notes

Reaction equation

HRID 571440 reaction equation
[C:1]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([OH:16])=O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:38][O:39][C:40](=[O:50])[C@H:41]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH2:42]>C1COCC1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:38][O:39][C:40](=[O:50])[C@H:41]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH:42][C:14](=[O:16])[CH2:13][NH:12][C:10](=[O:11])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acidHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 54341824Methyl Boc-glycylglycyl-L-phenylalaninateYield 93.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To N-Boc-glycylglycine (696 mg, 3.00 mmol, 1.00 equiv) in THF (10.0 mL) at 0° C. was added EDCI (1.15 g, 6.00 mmol, 2.00 equiv), HOBt (810 mg, 6.00 mmol, 2.00 equiv), n,n-diisopropylethyl amine (1.56 mL, 9.00 mmol, 3.00 equiv) and 4-(Dimethylamino)pyridine (36 mg, 0.030 mmol, 0.10 equiv) and L-phenylalanine methyl ester (647 mg, 3.00 mmol, 1.00 equiv). The reaction mixture was stirred for 1 hr at 0° C. and stirred for 12 h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water and dried (Na2SO4). The filtrate is concentrated in vacuo and the residue is purified by chromatography on silica gel eluting with DCM/MeOH 10:1 (v/v) to afford 1.10 g of the title compound as a colorless oil (93% yield).

Workup

  1. stirringstirred for 12 h at room temperature
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by chromatography on silica gel eluting with DCM/MeOH 10:1 (v/v)

Sources & evidence

ORD record
ord-aa99fb954c314011ad6fc93373dc5101
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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