Triethylamine → HCID 58619009, compound

HRID 1795074Notes

Reaction equation

HRID 1795074 reaction equation
[N:1]([C@@H:4]([CH:12]1[CH2:17][CH2:16][N:15]([C:18](OC(C)(C)C)=O)[CH2:14][CH2:13]1)[C:5](=[O:11])[N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)=[N+]=[N-].C(N(CC)CC)C.[I:32][C:33]1[CH:40]=[CH:39][C:36](CBr)=[CH:35][CH:34]=1>Cl.CO.C(Cl)Cl>[I:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:18][N:15]2[CH2:14][CH2:13][CH:12]([C@H:4]([NH2:1])[C:5](=[O:11])[N:6]3[CH2:10][CH2:9][S:8][CH2:7]3)[CH2:17][CH2:16]2)=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 9542584-Iodobenzyl bromideHCID 86592639HCID 86592639, compound

Product 1

HCID 58619009HCID 58619009, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[(1S)-1-azido-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]piperidine-1-carboxylate (Example 96, step B, 215 mg, 0.6 mmol) was dissolved in a freshly prepared HCl in methanol (1 mL acetyl chloride in 9 mL of methanol) and stirred for 4 h and concentrated to remove the Boc group. A portion of this material (29 mg, 0.1 mmol) was dissolved in methylene chloride (1 mL) and triethylamine (0.041 mL, 0.3 mmol) and 4-iodobenzylbromide (44 mg, 0.15 mmol) was added. The reaction mixture was stirred for 8 h, concentrated and purified by flash chromatography (silica gel, eluent: 20% acetone in CH2Cl2) to give the 4-iodobenzylamine. This material was dissolved in wet THF (10% water) and triphenyl phosphine (26 mg, 0.1 mmol) was added. The reaction mixture was heated in an oil bath at 60° C. for 3 h, concentrated and subjected to preparative TLC on silica gel (eluent: 10% MeOH in CH2Cl2) to afford 32 mg of the title compound. 1H NMR (500 MHz, CD3OD) δ 7.85 (d, 2H, J=6 Hz), 7.34 (d, 2H, J=6 Hz), 4.75–4.46 (m, 2H), 4.38–4.28 (m, 1H), 4.47 (s, 2H), 3.92–3.64 (m, 2H), 4.53 (bs, 2H), 3.16–3.02 (m, 4H), 2.19 (m, 1H), 1.98 (m, 2H), 1.83 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customto remove the Boc group
  3. stirringThe reaction mixture was stirred for 8 h
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel, eluent: 20% acetone in CH2Cl2)

Sources & evidence

ORD record
ord-b85cbbf5f5d543de8903404d8a306af4
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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