Diisopropylethylamine → HCID 178499331, compound

HRID 39297Notes

Reaction equation

HRID 39297 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]#[C:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)[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:42][C:43](=O)[O:44][CH:45]2[CH:52]3[CH:48]([O:49][CH2:50][CH2:51]3)[O:47][CH2:46]2)=CC=1)([O-])=O.CCN(C(C)C)C(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:27]#[C:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:21][CH2:22][CH:23]([NH:26][C:43]([O:44][CH:45]2[CH:52]3[CH:48]([O:49][CH2:50][CH2:51]3)[O:47][CH2:46]2)=[O:42])[CH2:24][CH2:25]1)[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 178499330HCID 178499330, compound

Product 1

HCID 178499331HCID 178499331, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[(4-amino-cyclohexyl)-(trans-4-methylcyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1ynyl)thiophene-2-carboxylic acid methyl ester (0.40 g, 0.873 mmol) in ACN (5.0 mL) was cooled to 0° C. and carbonic acid hexahydro-furo[2,3-b]furan-3-yl ester 4-nitro-phenyl ester (0.295 g, 1.0 mmol) was added, followed by DIEA (391 μL, 2.18 mmol) and DMAP (cat). The reaction mixture was warmed to rt, and stirred for 1 h. The solvent was removed under reduced pressure and the crude reaction mixture was partitioned between EtOAc and 2N K2CO3(aq). The layers were separated and the organics washed repeatedly with 2N K2CO3(aq). Both epimers of 5-(3,3-Dimethyl-but-ynyl)-3-[[4-(hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-cyclohexyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester were isolated by reverse phase HPLC and carried forward wet into the next reaction.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction mixture
  3. customwas partitioned between EtOAc and 2N K2CO3(aq)
  4. customThe layers were separated
  5. washthe organics washed repeatedly with 2N K2CO3(aq)

Sources & evidence

ORD record
ord-bf8f878b21a04d768ac4e1138c309520
Source dataset
uspto-grants-2013_09
Patent number
US08524764B2

Reaction notes

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