Diisopropylethylamine → (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-2-methoxy-benzylamide

HRID 2353604Notes

Reaction equation

HRID 2353604 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[NH2:47][CH2:48][C:49]1[CH:58]=[CH:57][C:52]([O:53][CH2:54][CH2:55][OH:56])=[CH:51][C:50]=1[O:59][CH3:60]>CN(C=O)C>[OH:56][CH2:55][CH2:54][O:53][C:52]1[CH:57]=[CH:58][C:49]([CH2:48][NH:47][C:12]([C:7]2[S:8][C:9]([CH3:11])=[C:10]3[C:6]=2[CH2:5][C@H:4]2[C:2]([CH3:1])([CH3:15])[C@H:3]23)=[O:14])=[C:50]([O:59][CH3:60])[CH:51]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57892448(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acidHCID 68453948HCID 68453948, compound

Product 1

HCID 11553135(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-2-methoxy-benzylamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (7.8 mg, 0.035 mmol), TBTU (11.2 mg, 0.035 mmol) and ethyl-diisopropylamine (18.0 μL, 0.105 mmol) in DMF (1 mL) is allowed to stand at rt for 30 min. The solution is added to 2-(4-aminomethyl-3-methoxy-phenoxy)-ethanol (6.4 mg, 0.035 mmol) and the mixture is allowed to stand at rt for 1 h. The mixture is separated by prep. HPLC to afford (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-2-methoxy-benzylamide (7.6 mg) as a colourless lyophilisate. LC-MS: tR=0.98 min, [M+1]+=402.16.

Workup

  1. waitto stand at rt for 1 h
  2. customThe mixture is separated by prep

Sources & evidence

ORD record
ord-53e9029bb43249518724fbe3ba2597b0
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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