Diisopropylethylamine → HCID 11509907, compound

HRID 2353608Notes

Reaction equation

HRID 2353608 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([O:23]N1N=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:59]=[CH:58][C:52]([O:53][CH:54](O)[CH2:55][CH3:56])=[CH:51][C:50]=1[O:60][CH3:61]>CN(C=O)C>[OH:23][CH2:56][CH2:55][CH2:54][O:53][C:52]1[CH:58]=[CH:59][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:60][CH3:61])[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 68454018HCID 68454018, compound

Product 1

HCID 11509907HCID 11509907, compoundYield 42.3%

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 (8.2 mg, 0.037 mmol), TBTU (11.9 mg, 0.037 mmol) and ethyl-diisopropylamine (19 μL, 0.111 mmol) in DMF (1 mL) is allowed to stand at rt for 30 min. The solution is added to 1-(4-aminomethyl-3-methoxy-phenoxy)-propanol (7.8 mg, 0.037 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-(3-hydroxy-propoxy)-2-methoxy-benzylamide (6.5 mg) as a colourless lyophilisate. LC-MS: tR=1.01 min, [M+1]+=416.12.

Workup

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

Sources & evidence

ORD record
ord-f288e394df024f4ab5aa86e2894c3137
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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