Hexane → HCID 58619002, compound

HRID 1795072Notes

Reaction equation

HRID 1795072 reaction equation
[N:1]([C@@H:4]([CH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1)[C:5](=[O:11])[N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)=[N+]=[N-].N([C@@H:23]([CH:31]1[CH2:36][CH2:35][CH:34](CO[Si](C(C)C)(C(C)C)C(C)C)[CH2:33][CH2:32]1)[C:24](N1CCSC1)=O)=[N+]=[N-].C([N:51]([CH2:54]C)CC)C.C(OCC)(=[O:58])C.[CH3:62][CH2:63][CH2:64][CH2:65]CC>C(Cl)Cl>[C:31]1([C:23]2[CH:24]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:32]=[CH:33][C:34]([NH:51][C:54](=[O:58])[O:19][CH2:18][CH:15]2[CH2:16][CH2:17][CH:12]([C@H:4]([NH2:1])[C:5](=[O:11])[N:6]3[CH2:10][CH2:9][S:8][CH2:7]3)[CH2:13][CH2:14]2)=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 91390783HCID 91390783, compoundHCID 131725689HCID 131725689, compound

Product 1

HCID 58619002HCID 58619002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 27 mg (0.095 mmol) of {4-[(1S)-1-azido-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]cyclohexyl}methanol from isomer II, Example 6, Step J in 1 mL of methylene chloride was added 20 mg (0.1 mmol) of 4-biphenylisocyanate and 0.02 mL of triethylamine. The mixture was stirred for 6 h and directly subjected to preparative TLC (silica gel, 45% ethyl acetate in hexane) to give the carbamate. The carbamate was dissolved in wet THF and to this solution was added 25 mg (excess) of triphenyl phosphine. The reaction mixture was heated at 60° C. for 3 h. Purification by preparative TLC on silica gel (eluent: 10% MeOH in CH2Cl2) gave the title compound. 1H NMR (500 MHz, CD3OD, HCl salt) δ 7.56–7.48 (m, 6H), 7.40 (t, 2H, J=7.5 Hz), 7.28 (t, 1H, J=6.0 Hz), 4.72 (m, 1H), 4.59 (d, 0.45H, J=9.2 Hz), 4.49 (d, 0.55H, J=9.2 Hz), 4.19 (d, 0.45H, J=5.9 Hz), 4.11 (d, 0.55H, J=5.9 Hz), 3.99 (d, 2H, J=6.3 Hz), 3.93 (m, 0.55H), 3.88 (m, 0.45H ), 3.76 (m, 1H), 3.2–3.05 (m, 2H), 1.98–1.80 (m, 5H), 1.71 (m, 1H), 1.27–1.09 (m, 4H).

Sources & evidence

ORD record
ord-87341026cbf44026a3b3b60e9c07d329
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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