Triethylamine → HCID 69601283, compound

HRID 891199Notes

Reaction equation

HRID 891199 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][N:5]1[CH2:11][C:10]([CH2:12]O)=[CH:9][CH2:8][CH:7]([NH:14][C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[O:16])[C:6]1=[O:27].C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][N:5]1[CH2:11][C:10]([CH2:12][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:9][CH2:8][CH:7]([NH:14][C:15]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[O:16])[C:6]1=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23598693HCID 23598693, compound

Product 1

HCID 69601283HCID 69601283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of {6-hydroxymethyl-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid methyl ester, 19, (1.35 g, 3.52 mmol) in 10 mL CH2Cl2is treated with triethyl amine (1.3 mL, 8.81 mmol) and methanesulfonyl chloride (0.61 mL, 7.93 mmol) at −78° C. After stirring at −78° C. for 2 hours, the reaction mixture is poured into a CH2Cl2/saturated NaCl solution. The organic layer is collected and washed with saturated NaHCO3, saturated NaCl, dried (Na2SO4) and concentrated in vacuo to afford the desired product which is used without further purification.

Workup

  1. customThe organic layer is collected
  2. washwashed with saturated NaHCO3, saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-756d1c4ce3f94e9ba4a7fb136739bb55
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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