Diisopropylethylamine → HCID 178499352, compound

HRID 336037Notes

Reaction equation

HRID 336037 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:25]#[C:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:8][C:9]=1[N:10]([C@@H:20]([CH3:24])[CH2:21][CH2:22][NH2:23])[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[N+](C1C=CC([O:40][C:41](=O)[O:42][CH:43]2[CH:50]3[CH:46]([O:47][CH2:48][CH2:49]3)[O:45][CH2:44]2)=CC=1)([O-])=O.C(N(C(C)C)CC)(C)C>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:25]#[C:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[CH:8][C:9]=1[N:10]([C@@H:20]([CH3:24])[CH2:21][CH2:22][NH:23][C:41]([O:42][CH:43]1[CH:50]2[CH:46]([O:47][CH2:48][CH2:49]2)[O:45][CH2:44]1)=[O:40])[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 22500062HCID 22500062, compoundHCID 178499350HCID 178499350, compound

Product 1

HCID 178499352HCID 178499352, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of crude 3-[[3-Amino-1-(S)-methyl-propyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester in ACN (3.0 mL) was treated with carbonic acid hexahydro-furo[2,3-b]furan-3-yl ester 4-nitro-phenyl ester (0.11 g, 0.375 mmol) followed by diisopropylethyl amine (0.1 mL, 0.625 mmol) and DMAP (cat). The reaction was stirred for 1 h and quenched with CH3OH (1 mL). Solvent was removed under reduced pressure and the crude material was partitioned between EtOAc, and ½ sat NaHCO3(aq). The organics were dried over Na2SO4, solids filtered and solvent removed under reduced pressure. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[3-(hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-1-(S)-methyl-propyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester was isolated by reverse phase HPLC and carried forward wet to the next reaction.

Workup

  1. customquenched with CH3OH (1 mL)
  2. customSolvent was removed under reduced pressure
  3. customthe crude material was partitioned between EtOAc, and ½
  4. dry with materialThe organics were dried over Na2SO4, solids
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-e314c9e38ec04c9e87f389f2bc931f16
Source dataset
uspto-grants-2014_11
Patent number
US08884030B2

Reaction notes

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