Triethylamine → HCID 69584372, compound

HRID 1824440Notes

Reaction equation

HRID 1824440 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][CH:14]1[C:21](=[O:22])[N:20]2[CH:23]([C:26]([OH:28])=O)[CH2:24][CH2:25][CH:19]2[CH2:18][CH:17]=[CH:16][CH2:15]1)=[O:12].CCN=C=NCCCN(C)C.[NH2:40][CH:41]([CH2:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C:42](=[O:55])[CH2:43][O:44][C:45](=[O:54])[C:46]1[C:51]([CH3:52])=[CH:50][CH:49]=[CH:48][C:47]=1[CH3:53].C(N(CC)CC)C>ClCCl>[C:60]([O:59][C:57]([CH2:56][CH:41]([NH:40][C:26]([CH:23]1[N:20]2[C:21](=[O:22])[CH:14]([NH:13][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[O:12])[CH2:15][CH:16]=[CH:17][CH2:18][CH:19]2[CH2:25][CH2:24]1)=[O:28])[C:42](=[O:55])[CH2:43][O:44][C:45](=[O:54])[C:46]1[C:47]([CH3:53])=[CH:48][CH:49]=[CH:50][C:51]=1[CH3:52])=[O:58])([CH3:63])([CH3:61])[CH3:62]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 235714112,6-Dimethyl-benzoic acid 3-amino-4-tert-butoxycarbonyl-2-oxo-butyl esterHCID 69584313HCID 69584313, compound

Product 1

HCID 69584372HCID 69584372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid, (124 mg, 0.33 mmol)in dichloromethane is added EDCI (191 mg, 1 mmol), 2,6-dimethyl-benzoic acid 3-amino-4-tert-butoxycarbonyl-2-oxo-butyl ester, 111, (200 mg, 0.62 mmol), and triethylamine (150 ul). After consumption of the starting material, the reaction is washed with 1N HCl (1×50 ml), water (1×50 ml), and brine (1×50 ml). The CHCl2 is reduced in vacuo. The residue is used directly in the next step without purification. ESI MS 696.1 (M+H).

Workup

  1. customAfter consumption of the starting material
  2. washthe reaction is washed with 1N HCl (1×50 ml), water (1×50 ml), and brine (1×50 ml)
  3. customThe residue is used directly in the next step without purification

Sources & evidence

ORD record
ord-fec5b9e3aa1d47a79127774db1d5d37f
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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