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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-BOC-4-aminobenzoyl methionine methyl ester

HRID 356076
Notes
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Reaction equation

HRID 356076 reaction equation
[C:1](NC1C=CC(C(O)=O)=CC=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:19][O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH2:25][S:26][CH3:27])[NH2:23].CCN=C=N[CH2:34][CH2:35][CH2:36][N:37](C)C.[OH:40][C:41]1C2N=NNC=2[CH:44]=[CH:43][CH:42]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:19][O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH2:25][S:26][CH3:27])[N:23]([C:41](=[O:40])[C:42]1[CH:34]=[CH:35][C:36]([NH2:37])=[CH:44][CH:43]=1)[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acidHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 67564255N-BOC-4-aminobenzoyl methionine methyl esterYield 71.3%

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Into a dried, nitrogen filled flask was placed N-BOC-4-aminobenzoic acid (8.77 g, 36.97 mmol) in dry CH2Cl2 (148 ml) along with methionine methyl ester hydrochloride (8.12 g, 40.66 mmol). This solution was cooled in an ice bath and triethylamine (6.7 ml), EDCI (7.80 g, 40.66 mmol) and hydroxybenzotriazole (HOBT, 5.50 g, 40.66 mmol) were added. The mixture was stirred overnight, diluted with more CH2Cl2 and was extracted 3 times each with 1M HCl, 1M NaHCO3 and water. The CH2Cl2 was dried over MgSO4 and the solvent was removed in vacuo. The solid was recrystallized from ethyl acetate/ hexanes to yield 9.72 g (71.3%) of pure product. mp 184°-185° C.; 1H NMR (CDCl3) 1.53 (9 H, s), 2.06-2.18 (4 H, m), 2.23-2.33 (1 H, m), 2.59 (2 H, t, J=7.6 Hz), 3.80 (3 H, s), 4.92 (1 H, m), 7.45 (2 H, d, J=8.7 Hz), 7.77 (2 H, d, J=8.7 Hz); 13C NMR (CDCl3) 15.59, 28.34, 30.15, 31.64, 52.10, 52.73, 81.20, 117.73, 127.8, 128.33, 141.88, 152.33, 166.50, 172.75; anal. calc. for C18H26N2O5S, C: 56.53, H: 6.85, N: 7.29; found, C: 56.47, H: 6.86, N: 7.29; m/ z (EI) 382 (M).

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. extractionwas extracted 3 times each with 1M HCl, 1M NaHCO3 and water
  3. dry with materialThe CH2Cl2 was dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe solid was recrystallized from ethyl acetate/ hexanes

Sources & evidence

ORD record
ord-60dd2c7aacd54c3396cf200f3ec45eeb
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834434

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes