Triethylamine → HCID 11556815, compound

HRID 1433118Notes

Reaction equation

HRID 1433118 reaction equation
[C:1]([CH2:29][NH:30][C@H:31]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([C:22]([C:25]([F:28])([F:27])[F:26])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].ClC([O:50][CH2:51][CH3:52])=O.[CH2:53](N(CC)CC)C>C(Cl)Cl>[C:1]([CH2:29][NH:30][C@H:31]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([O:39][C:51]([CH2:52][CH3:53])=[O:50])=[CH:37][CH:38]=1)([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([C:22]([C:25]([F:26])([F:27])[F:28])([F:23])[F:24])([F:20])[F:21])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11527754HCID 11527754, compound

Product 1

HCID 11556815HCID 11556815, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

C9F19CH2NH-Tyr-OBut (287 mg, 0.4 mmol), ethyl chloroformate (42 microL, 0.44 mmol) and triethylamine (70 μL, 0.5 mmol) were stirred in CH2Cl2 (5 mL) at room temperature for 1 hr. The mixture was diluted with CH2Cl2 (30 ml), extracted with 2×30 mL 0.1 M citric acid. The organic phase was dried and evaporated to yield 286 mg (92%) of the desired C9F19CH2NH-Tyr(OCOEt)-OBut, pure by NMR. 1H NMR (CDCl3, 300 MHz, ref. TMS=0 ppm) 1.4 (overlapping s, 9H, But and t, 3H, OCH2CH3), 2.8 (m, 2H, tyrosine CH2), 3.0-3.4 (ABX3, m, 2H, RfCF2CH2), 3.4 (t, 1H), 4.3 (q, 2H, OCH2CH3), 6.7 (d, 2H), 7.0 (d, 2H).

Workup

  1. extractionextracted with 2×30 mL 0.1 M citric acid
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-19d2cf12c91b43d5b2b02e5b2f1e61c0
Source dataset
uspto-grants-2009_11
Patent number
US07612166B2

Reaction notes

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